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[ CAS No. 6574-15-8 ] {[proInfo.proName]}

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Chemical Structure| 6574-15-8
Chemical Structure| 6574-15-8
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Product Details of [ 6574-15-8 ]

CAS No. :6574-15-8 MDL No. :MFCD00023662
Formula : C11H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SGPLAXFUDTWHRS-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :81049
Synonyms :

Calculated chemistry of [ 6574-15-8 ]      Expand+

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 : 49.06 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 3.26
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 1.46
Log Po/w (SILICOS-IT) : 0.33
Consensus Log Po/w : 1.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.095 mg/ml ; 0.000461 mol/l
Class : Soluble
Log S (Ali) : -3.96
Solubility : 0.0224 mg/ml ; 0.000109 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.64 mg/ml ; 0.0031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 6574-15-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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   1~4

  • 1
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  • [ 6574-15-8 ]
  • 2
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  • [ 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
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  • [ 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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