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Chemical Structure| 6574-15-8 Chemical Structure| 6574-15-8

Structure of 6574-15-8

Chemical Structure| 6574-15-8

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CAS No.: 6574-15-8

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Product Details of [ 6574-15-8 ]

CAS No. :6574-15-8
Formula : C11H14N2O2
M.W : 206.24
SMILES Code : C1=CC(=CC=C1N2CCCCC2)[N+](=O)[O-]
MDL No. :MFCD00023662
InChI Key :SGPLAXFUDTWHRS-UHFFFAOYSA-N
Pubchem ID :81049

Safety of [ 6574-15-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 6574-15-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.45
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 64.71
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

49.06 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.01
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.26
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.2
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.46
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.33
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.85

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.34
Solubility 0.095 mg/ml ; 0.000461 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.96
Solubility 0.0224 mg/ml ; 0.000109 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.51
Solubility 0.64 mg/ml ; 0.0031 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.24 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

1.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.68

Application In Synthesis of [ 6574-15-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6574-15-8 ]

[ 6574-15-8 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 110-89-4 ]
  • [ 98-95-3 ]
  • [ 6574-15-8 ]
  • 2
  • [ 110-89-4 ]
  • [ 100-00-5 ]
  • [ 6574-15-8 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate; In neat (no solvent); at 120℃; for 24h; General procedure: In a conical flask (10 mL) a mixture of aryl halide (1 mmol),amine (3 mmol), K2CO3 (2 mmol), and Pd-PFMN catalyst (0.06 g, 1.2 mol%) was stirred for 24 h. Afterward, themixture was cooled down to room temperature and the catalystwas magnetically separated from the reaction mixtureand washed with diethyl ether (2 × 10 mL) followed bydeionized and oxygen-free water (2 × 10 mL). The reusedcatalyst was dried for the next run. The aqueous phase wasextracted with diethyl ether (2 × 10 mL) and the combinedorganic phases were dried over Na2SO4. The products werepurified by column chromatography (hexane/ethyl acetate)to obtain the desired purity.
93% With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 23h; A mixture of piperidine (7.42 mL,0.075 mol), 4-chloronitrobenzene 9 (11.82 g, 0.075 mol) and K2CO3(10.37 g, 0.075 mol) in DMSO (50 mL) was heated at 120 C for 23 hwith stirring. The reaction was cooled to r.t., then 1:1 EtOH:H2O(200 mL) added. The resulting precipitatewas collected by filtrationand dried to give the title compound 15 (14.45 g, 93%) as an orangesolid which was used without further purification. m.p. 99-101 C(Lit [24]. 101-102.5 C) The 1H NMR data were in agreement withliterature values [25]. deltaH (400 MHz; CDCl3) 1.67-1.70 (6H, m, H-30 ,H-40), 3.43 (4H, s, H-20), 6.79 (2H, d, J 9.5 Hz, H-2), 8.10 (2H, d,J 9.5 Hz, H-3).
86% With solid-supported nano and microparticles of Pd(0); In N,N-dimethyl-formamide; at 80℃; for 6h; General procedure: A mixture of 4-nitrochlorobenzene (100 mg, 0.63 mmol), piperidine (63.86 mg, 0.75 mmol) and SS-Pd (284.5 mg, 0.01 mmol of Pd) in DMF was placed in round bottom flask. The reaction mixture was then heated at 80oC under magnetic stirring for 6h. The completion of reaction was monitored by TLC. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate three times. The combined organic layer was concentrated to yield the crude product, which was purified by silica gel column chromatography (hexane:EtOAc :: 90:10) to yield 1-(4-nitrophenyl)piperidine 22 as a yellowish solid (112 mg, 86%), mp 104-105 oC; 1H NMR (300 MHz, CDCl3-d1) delta 1H NMR (300 MHz, CDCl3-d1) delta 8.05-8.09( m, 2H), 6.76-6.79( m, 2H), 3.43 (m, 4H), 1.68 (m, 6H) ; 13C NMR (75 MHz, CDCl3-d1) delta 155.28, 137.70, 126.27 (2C), 112.20 (2C), 48.72 (2C), 25.66 (2C), 24.61; HRMS (ESI) data: m/z calcd for [M+ H]+ C11H15N2O2 207.2490, obsd. 207.2472.
85% In neat (no solvent); at 30℃; for 0.25h;Green chemistry; General procedure: To a solution of amine (1.2 mmol) dissolved in 20% DES,aryl halide (1 mmol) was added at room temperature andstirred for appropriate time. The progress of the reactionwas monitored by TLC. After completion of the reactioncold water was added to the reaction mixture. The precipitatedsolid was filtered off, and recrystallized using ethanol.
63% With water; sodium t-butanolate; In toluene; at 105℃; for 20h;Schlenk technique; General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA-Pd (0.05 g, 0.04 mmol, 1.5 mol%), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.
600 mg With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 100℃; General procedure: 1-Chloro-4-nitrobenzene (500 mg, 3.17 mmol) and K2CO3 (526 mg, 3.8 mmol, 1.2 equiv.) were added together with DMF (10 mL) and stirred at RT. Morpholine (440 muL, 5.1 mmol, 1.6 equiv.) was added to the reaction mixture which was heated at 100 C overnight. After cooling down to RT, the mixture was extracted with EA. The EA layer was washed with DI-water three times and the combined water layers were back-extracted with EA three times. The combined EA extracts were dried (Na2SO4) and all solvent was evaporated under vacuum. The residue was purified by flash chromatography (elution system - EA : Hexane = 1 : 1 ) to give the title compound as a yellow solid (294 mg, 1.41 mmol).

  • 3
  • [ 110-89-4 ]
  • [ 350-46-9 ]
  • [ 6574-15-8 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In dimethyl sulfoxide; at 90℃; for 9h; 4-Fluoronitrobenzene (323 mg, 2.3 mmol) was dissolved in DMSO (5 ml), potassium carbonate (475 mg, 3.5 mmol) and piperidine (460 mul, 4.6 mmol) were added, and the mixture was stirred at 90 C. for 9 hr. Then, water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with saturated aqueous NaCl. The organic layer was dried over Na2CO3, the solvent was evaporated to give compound Y197 (yield; 472 mg, 100%). Compound Y197 was dissolved in ethyl acetate (20 ml), Pd/C (186 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. Then, the reaction solution was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (40:1)) to give compound Y222 (yield, quantitative, 394 mg). Compound Y491 (mentioned later) (80 mg, 0.18 mmol) was dissolved in dichloromethane (2 ml), compound Y222 (100 mg, 0.58 mmol) was added, and the mixture was stirred at room temperature for 5 hr. Then, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (35:1)) to give the title compound (yield; 68 mg, 64%). 1H NMR (500 MHz, CDCl3) delta8.40 (s, 1H), 8.0 (d, 1H, J=8.0 Hz), 7.70 (d, 1H, J=8.5 Hz), 7.52 (dd, 1H, J=8.0, 7.5 Hz), 6.92 (dd, 2H, J=9.0, 3.5 Hz), 6.77 (dd, 2H, J=9.0, 6.5 Hz), 5.33 (t, 1H, J=6.0 Hz), 4.07 (bs, 2H), 3.11-3.09 (m, 4H), 2.79-2.64 (m, 4H), 1.69-1.53 (m, 10H), 1.43 (s, 9H), 1.09-1.01 (m, 2H) 13C NMR (125 MHz, CDCl3) delta154.9, 141.6, 140.8, 131.4, 130.9, 129.8, 125.8, 125.7, 79.7, 77.4, 48.7, 36.6, 29.6, 28.6, 25.7, 24.2 HRMS (FAB-) m/z: [M-H]- calcd for C28H39N4O6S2, 591.2311. found, 591.2324
97% With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 20h; In a 250mL round-bottom flask equipped with a stirring bar, a mixture of 12.8g (0.15mol) of piperidine, 21.2g (0.15mol) of 4-fluoronitrobenzene, and 20.7g (0.15mol) of potassium carbonate (K2CO3) in 100mL of dimethyl sulfoxide (DMSO) was heated with stirring at 120C for 20h. After cooling, the mixture was poured into 400mL mixed solution of ethanol/water (1:1). The yellow crystals were collected by filtration with a yield of 30.0g (97%) and a melting point of 100-102C, measured by differential scanning calorimetry (DSC) at a scan rate of 10C/min. IR (KBr):1577, 1329cm-1 (-NO2 str.). 1H NMR (500MHz, DMSO-d6, delta, ppm): 8.02 (d, J=9.5Hz, 2H, He), 6.98 (d, J=9.5Hz, 2H, Hd), 3.49 (t, J=5.7Hz, 4H, Hc), 1.63 (m, 2H, Ha), 1.57 (m, 4H, Hb). 13C NMR (125MHz, DMSO-d6, delta, ppm): 154.5 (C4), 135.9 (C7), 125.8 (C6) 112.2 (C5), 47.5 (C3), 24.8 (C2), 23.8 (C1)
75% In dimethyl sulfoxide; at 80℃; for 20h; Synthesis of 1-(4-Nitro-phenyl)-piperidine Piperidine (362 mg, 0.2 mmol) was added to a solution of 1-fluoro-4-nitro-benzene (200 mg, 1.4 mmol) in DMSO (10 mL) and the mixture was stirred at 80 C. for 20 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 220 mg (75%) of 1-(4-nitro-phenyl)-piperidine.
54% With potassium hydroxide; In dimethyl sulfoxide; at 80℃; for 16h; General procedure: A mixture of 2-fluorobenzamide (1a, 69.5 mg, 0.5 mmol), MeOH (ca. 32.0 mg, 1.0 mmol), KOH (56.0 mg, 1.0 mmol) and DMSO (2.0 mL) in a 25 mL screw-capped thick-walled Pyrex tube was stirred at room temperature for 16 h, and then water (10 mL) was added to the reaction mixture with stirring, and the mixture was extracted with ethyl acetate three times (3 * 10 mL). The combined organic phases were dried over Na2SO4 overnight. The filtered solution was concentrated under reduced pressure, and the crude residue was purified by column chromatography on silica gel with the use of petroleum ether/ethyl acetate/trimethylamine (gradient mixture ratio from 6:1:0.05 to 2:1:0.05 in volume) to afford 2aa as a white solid in 80% yield (60.7 mg).
46% With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 5h;Inert atmosphere; Step Reaction: 15.0g equipped with a mechanical stirring was added a 500mL three-necked flask (176mmol)Piperidine, 24.9g (176mmol) of fluoro nitrobenzene, 24.5g (176mmol) of potassium carbonate was added 250mLOf N, N- dimethylformamide as the solvent, with stirring, under nitrogen, the reaction at 110 5H, coldAfter cooling, ice water discharge, the crude product was washed with water three times, dried, and recrystallized from ethanol to give yellowPiperidin-4-nitrophenyl powder 16.7g, 46% yield;
With sodium hydrogencarbonate; In N-methyl-acetamide; water; ethyl acetate; (1) A solution of p-fluoronitrobenzene (31.8 ml) in dimethylformamide (200 ml) was ice-cooled and to this was added piperidine (60 ml) dropwise, followed by stirring with ice cooling for 2 hours. After the solvent was distilled off, the residual oily product was dissolved in ethyl acetate ester (200 ml), followed by washing in turn with aqueous saturated solution of sodium bicarbonate and water. Then, the solution was dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was recrystallized from n-hexane to obtain N-(4-nitrophenyl)piperidine as yellow crystals (52.8 g).
With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 100℃; for 48h; A solution of 4-fluoronitrobenzene (1.41 g, 1.06 mL, O. OLMOL), N, N- diisopropylethylamine (1.1 equiv), and amine (1.1 equiv) IN N, N-DIMETHYLFORM- amide (8-10 mL) was heated at 100 C for 48 h in a sealed tube. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0 to 10% methanol-dichloromethane) to afford the nitroaniline
With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 100℃; for 48h; Method K; General method for the synthesis of 4-aminoanilines of type K.; Step 1:; A solution of 4-fluoronitrobenzene (1.41 g, 1.06 mL, O. Olmol), N, N- diisopropylethylamine (1.1 equiv), and amine (1.1 equiv) inN, N-dimethylform- amide (8-10 mL) was heated at 100 C for 48 h in a sealed tube. The reaction mixture was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0 to 10% methanol-dichloromethane) to afford the nitroaniline.
With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; General procedure: Substituted amine (1.2 equiv) was added to a mixture of 4-fluoronitrobenzene (1 equiv) and K2CO3 (2.0 equiv) in DMF (7mL/g). The reaction mixture was stirred at 40C and followed by TLC. After completion of the reaction, the mixture was poured into stirring ice-water. The resulting precipitate was filtered and dried to obtain compounds 11 as a yellow solid.
With potassium carbonate; In dimethyl sulfoxide; at 0 - 80℃; for 8h; General procedure: To a solution of 1-fluoro-4-nitrobenzene (5 g, 35.5 mmol) in DMSO(100 mL) was added K2CO3 (14.6 g, 106.4 mmol) at room temperature.And a solution of tert-butyl piperazine-1-carboxylate (3.5 g, 35.5 mmol)in DMSO (50 mL) was added dropwise to the mixture at 0 C. The reactionmixture was stirred at 80 C for 8 h. Water (500 mL) was added toquench the reaction. The precipitated solid was collected on a filter anddried under reduced pressure to give 1a (8.0 g, yield 73.5%) withoutfurther purification. MS m/z: 308.2 [M+H]+. The crude product wasdelivered directly to the next step.

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[11]Patent: CN105503775,2016,A .Location in patent: Paragraph 0040; 0041.
[12]Bulletin de la Societe Chimique de France,1956,p. 311,315.
[13]Organic Magnetic Resonance,1982,vol. 18,p. 104 - 108.
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[17]Chemical Communications,2005,p. 2857 - 2859.
[18]Patent: US5580883,1996,A .
[19]Patent: WO2005/9978,2005,A1 .Location in patent: Page 99; 101.
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  • 5
  • [ 6574-15-8 ]
  • [ 74-88-4 ]
  • 1-methyl-1-(4-nitro-phenyl)-piperidinium; iodide [ No CAS ]
  • 6
  • [ 6574-15-8 ]
  • 4-piperidino-cyclohexylamine [ No CAS ]
  • 7
  • [ 6574-15-8 ]
  • [ 2359-60-6 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20℃; for 3h; 4-Fluoronitrobenzene (323 mg, 2.3 mmol) was dissolved in DMSO (5 ml), potassium carbonate (475 mg, 3.5 mmol) and piperidine (460 mul, 4.6 mmol) were added, and the mixture was stirred at 90 C. for 9 hr. Then, water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with saturated aqueous NaCl. The organic layer was dried over Na2CO3, the solvent was evaporated to give compound Y197 (yield; 472 mg, 100%). Compound Y197 was dissolved in ethyl acetate (20 ml), Pd/C (186 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. Then, the reaction solution was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (40:1)) to give compound Y222 (yield, quantitative, 394 mg). Compound Y491 (mentioned later) (80 mg, 0.18 mmol) was dissolved in dichloromethane (2 ml), compound Y222 (100 mg, 0.58 mmol) was added, and the mixture was stirred at room temperature for 5 hr. Then, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluent; chloroform:methanol (35:1)) to give the title compound (yield; 68 mg, 64%). 1H NMR (500 MHz, CDCl3) delta8.40 (s, 1H), 8.0 (d, 1H, J=8.0 Hz), 7.70 (d, 1H, J=8.5 Hz), 7.52 (dd, 1H, J=8.0, 7.5 Hz), 6.92 (dd, 2H, J=9.0, 3.5 Hz), 6.77 (dd, 2H, J=9.0, 6.5 Hz), 5.33 (t, 1H, J=6.0 Hz), 4.07 (bs, 2H), 3.11-3.09 (m, 4H), 2.79-2.64 (m, 4H), 1.69-1.53 (m, 10H), 1.43 (s, 9H), 1.09-1.01 (m, 2H) 13C NMR (125 MHz, CDCl3) delta154.9, 141.6, 140.8, 131.4, 130.9, 129.8, 125.8, 125.7, 79.7, 77.4, 48.7, 36.6, 29.6, 28.6, 25.7, 24.2 HRMS (FAB-) m/z: [M-H]- calcd for C28H39N4O6S2, 591.2311. found, 591.2324
99% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 0.59 mL (6 mmol) piperidine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 50:1, 30:1) to afford 902 mg (87%) yellow solid. The solid was dissolved in methanol, 90 mg Pd-C (10%) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentratedin vacuo. The crude product was purified by flash chromatography (PEEA = 5:1) to afford 4l? 0.706 g 99%.
96% Synthesis of 4-Piperidin-1-yl-phenylamine Ammonium chloride (228 mg, 4.2 mmol) in water (4 mL) was added to a solution of 1-(4-nitro-phenyl)-piperidine (220 mg, 1.0 mmol) in THF (6 mL) and the resulting mixture was stirred at 75 C. for 30 minutes. Iron powder (238 mg, 4.2 mmol) was then added portion wise and the mixture stirred for 5 hours at 75 C. The reaction mixture was filtered over celite, the filtrate was basified with sodium bicarbonate solution and the product extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 180 mg (96%) of 4-Piperidin-1-yl-phenylamine. LCMS: 177.13 (M+1)+, 80.6%, 1H NMR: (DMSO-d6): delta 6.67 (m, 2H), 6.47 (m, 2H), 4.51 (s, 2H), 2.57 (t, 4H), 1.6 (q, 4H), 1.49 (m, 2H)
85% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 23h; To a solution of <strong>[6574-15-8]1-(4-nitrophenyl)piperidine</strong> 15 (5.67 g, 0.028 mol) in EtOH (150 mL) was added 10%Pd/C (0.586 g, 10% w/w). The resulting mixture was stirred at roomtemperature under an atmosphere of hydrogen for 23 h. Aftercompletion, the mixture was filtered through Celite and washedwith EtOH. The solvent was removed in vacuo to afford a red oilwhich was extracted with DCM (3 x 10 mL) and washed with brine.The combined organic extracts were dried (MgSO4) and the solventwas removed in vacuo to give the title compound 18 (4.12 g, 85%) as ared oil which was used without further purification. deltaH (400 MHz;CDCl3) 1.51-1.57 (2H, m, H-40), 1.70-1.75 (4H, m, H-30), 3.00 (4H, t,J 5.5 Hz, H-20), 3.41 (2H, s, NH2), 6.63 (2H, d, J 8.8 Hz, H-2), 6.83(2H, d, J 8.8 Hz, H-3). deltaC (100 MHz; CDCl3) 24.2 (C-40), 26.2 (C-30),52.6 (C-20), 116.2 (C-2), 119.1 (C-3), 139.8 (C-1), 145.8 (C-4); IR numax(ATR)/cm-1: 3336, 2930, 2851, 1620, 1509, 1229, 819; m/z(ESI+): 259 (71%), 177 (100%); HRMS (ESI+) found (MH+): 177.1380,C11H17N2 requires 177.1386. The 1H NMR data were in agreementwith literature values [26].
80% With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; for 12h;Reflux; The second step: to install a magnetic stir, thermometer, condenser 500mL three-necked flask is addedThe first step in the reaction of 15.0g of 4-nitrophenyl piperidine powder, 2.0g of 10% mass fraction of Pd / C,180mL of ethanol was added as a solvent, and stirred to obtain a uniform suspension. After heating to reflux, the suspensionWas slowly added dropwise 45.0g of mass fraction of 80% hydrazine hydrate solution, stirring continued at reflux for 12h. The reaction was completeCompleted, the reaction solution was filtered hot to remove Pd / C, the filtrate was concentrated under reduced pressure to 1/4 of its original volume, under a nitrogen atmosphereCooling and crystallization, to obtain a gray 4-aminophenyl-piperidine 10.2 g of crystals, 80% yield;
75% With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; for 10h;Reflux; In a 500mL round-bottom flask, 28.3g (0.14mol) of nitro compound 1, 0.2g of 10 wt% Pd/C, 20mL hydrazine monohydrate and 180mL of ethanol was stirred at a reflux temperature for 10h. The solution was filtered hot to remove Pd/C, and the filtrate was evaporated under reduced pressure to dryness. A deep purplish red liquid was obtained. The product (2) was used for the next step without further purification. The yield was 18.1g (75%). IR (KBr): 3429, 3346cm-1 (-NH2 str.). 1H NMR (500MHz, DMSO-d6, delta, ppm): 6.66 (d, J=8.8Hz, 2H, He), 6.48 (d, J=8.8Hz, 2H, Hd), 4.49 (s, 2H, -NH2), 2.84 (t, J=5.4Hz, 4H, Hc), 1.59 (m, 4H, Hb), 1.45 (m, 2H, Ha). 13C NMR (125MHz, DMSO-d6, delta, ppm): 143.5 (C4), 141.9 (C7), 118.6 (C6), 114.7 (C5), 52.1 (C3), 25.8 (C2), 23.8 (C1)
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; 10% Palladium on carbon (0.05 g) was added to a solution of the nitroaniline (0.001 mol) in ethanol (50 mL) under a H2 (g) atmosphere (via balloon). The reaction mixture stirred at r. t. overnight and was then filtered through celite. The filtrate was concentrated to afford a dark yellow oil.
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; Step 2:; 10% Palladium on carbon (0.05 g) was added to a solution of the nitroaniline (0.001 mol) in ethanol (50 mL) under a H2 (g) atmosphere (via balloon). The reaction mixture stirred at r. t. overnight and was then filtered through celite. The filtrate was concentrated to afford a dark yellow oil.
384 mg With iron; ammonium chloride; In methanol; water; at 100℃; General procedure: The compound S1 (261 mg, 1.25 mmol), iron powder (210 mg, 4.76 mmol, 3 equiv.) and ammonium chloride (335 mg, 6.27 mmol, 5 equiv.) were dissolved in methanol : water (2 : 1, 15 mL). The reaction mixture was heated at 100 C overnight, cooled to RT, filtered through celite and the solvent was reduced under vacuum. The condensed mixture was extracted with DCM, washed with brine, dried with sodium sulfate and all solvent was evaporated to furnish the condensed residue, which was purified by flash chromatography (elution system - EA/Hexane = 1 : 1 ) to obtain the title compound (245 mg, 1.43 mmol).
With 5%-palladium/activated carbon; hydrogen; In ethanol; water; at 20℃; General procedure: The substituted nitro compound 11 (1 equiv in a mixture of EtOH-H2O, 95:5, 20mL) was treated with 10% Pd-carbon (5% w/w). The reaction was subjected to hydrogenation under hydrogen gas at room temperature and the reaction was monitored by TLC. After completion of the reaction, the mixture was filtered through a Celite bed and concentrated in a vacuum to afford product 12.
With FeO(OH)/C; hydrazine hydrate; In ethanol; at 0 - 80℃; for 4h; General procedure: To a solution of 1a (5 g, 22.5 mmol) in 95% ethanol (100 mL) wasadded goethite (FeO(OH))/C (1.0 g) at room temperature. And a solution of 80% hydrazine hydrate (25 mL, 400 mmol) in 95% ethanol (50 mL) was added dropwise to the mixture at 0 C. The reaction mixture was stirred at 80 C for 4 h. The solvent was removed in vacuo to give 2a (3.8 g, yield 74.5%). MS m/z: 278.2 [M+H]+.

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  • [ 111-24-0 ]
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  • [ 6574-15-8 ]
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  • [ 110-89-4 ]
  • [ 636-98-6 ]
  • [ 6574-15-8 ]
YieldReaction ConditionsOperation in experiment
95% With sodium acetate; In N,N-dimethyl-formamide; at 130℃; for 8h;Aerobic conditions; General procedure: A mixture of 1-iodo-4-nitro-benzene (1 mmol, 249 mg), pyrrolidine (2 mmol, 142 mg), Pd-MCM-48 (30 mg) and NaOAc (2 mmol, 164 mg) was heated at 130 C in DMF (5 mL) for 12 h till completion of reaction (TLC). The reaction mixture was cooled to room temperature and catalyst was separated by filtration. The filtrate was extracted with ethyl acetate (20 mL), washed with water (5×1 mL), dried over Na2SO4. The solvent was evaporated to leave the crude product, which was purified by column chromatography over silica-gel (2% ethyl acetate in hexane) to provide pure 1-(4-nitro-phenyl)-pyrrolidine (153 mg, 80%). All the products listed in Table 3 are known in the literature and gave 1H and 13C NMR data consistent with the structures and data in the literature.
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  • [ 120952-12-7 ]
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  • [ 6574-15-8 ]
  • [ 40832-54-0 ]
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  • [ 42106-50-3 ]
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  • [ 6574-15-8 ]
YieldReaction ConditionsOperation in experiment
97% With D-myo-inositol; copper; caesium carbonate; In water; at 100℃; The reaction of 1-bromo-4-nitrobenzene (0.20g, 1.0 mmol), piperidine (0.128 g, 1.5 mmol), copper powder (0.0064 g, 0.1 mmol),MI (0.036 g, 0.2 mmol), Cs2CO3 (0.720 g, 2.2 mmol), TBAHS (0.068 g, 0.2 mmol)produced 0.199 g (97%) of 1-(4-nitrophenyl)piperidine as a yellow solid.
87% With potassium carbonate; In N,N-dimethyl-formamide;Reflux; A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 0.59 mL (6 mmol) piperidine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 50:1, 30:1) to afford 902 mg (87%) yellow solid. The solid was dissolved in methanol, 90 mg Pd-C (10%) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentratedin vacuo. The crude product was purified by flash chromatography (PEEA = 5:1) to afford 4l? 0.706 g 99%.
80% With sodium acetate; In N,N-dimethyl-formamide; at 130℃; for 8h;Aerobic conditions; General procedure: A mixture of 1-iodo-4-nitro-benzene (1 mmol, 249 mg), pyrrolidine (2 mmol, 142 mg), Pd-MCM-48 (30 mg) and NaOAc (2 mmol, 164 mg) was heated at 130 C in DMF (5 mL) for 12 h till completion of reaction (TLC). The reaction mixture was cooled to room temperature and catalyst was separated by filtration. The filtrate was extracted with ethyl acetate (20 mL), washed with water (5×1 mL), dried over Na2SO4. The solvent was evaporated to leave the crude product, which was purified by column chromatography over silica-gel (2% ethyl acetate in hexane) to provide pure 1-(4-nitro-phenyl)-pyrrolidine (153 mg, 80%). All the products listed in Table 3 are known in the literature and gave 1H and 13C NMR data consistent with the structures and data in the literature.
41% With water; sodium t-butanolate; In toluene; at 105℃; for 20h;Schlenk technique; General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA-Pd (0.05 g, 0.04 mmol, 1.5 mol%), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.
With potassium carbonate; In water; dimethyl sulfoxide; EXAMPLE 12 Acridin-9-yl-[4-(piperidin-1-yl)phenyl]amine 0.202 g (1.0 mmol) of 1-bromo-4-nitrobenzene and 0.20 ml of piperidine (2.0 mmol) were dissolved in 3 ml of dimethylsulfoxide. 0.207 g (1.5 mmol) of potassium carbonate was added and the reaction mixture was heated to 100 C. After 2 h 100 ml of water was added, and the mixture was extracted a few times with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to obtain crude 4-(piperidin-1-yl)-1-nitrobenzene.

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  • sodium amide [ No CAS ]
  • [ 98-95-3 ]
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  • N-<4-nitro-2-amino-phenyl>-piperidine [ No CAS ]
  • [ 6574-15-8 ]
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  • [ 110-89-4 ]
  • <i>p</i>-halogen-nitrobenzole [ No CAS ]
  • [ 6574-15-8 ]
 

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