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Chemical Structure| 1131-01-7 Chemical Structure| 1131-01-7

Structure of 1131-01-7

Chemical Structure| 1131-01-7

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CAS No.: 1131-01-7

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Product Details of [ 1131-01-7 ]

CAS No. :1131-01-7
Formula : C10H12ClNO
M.W : 197.66
SMILES Code : C1=CC=C(C(=C1C)NC(CCl)=O)C
MDL No. :MFCD00000926
InChI Key :FPQQSNUTBWFFLB-UHFFFAOYSA-N
Pubchem ID :70798

Safety of [ 1131-01-7 ]

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

Computational Chemistry of [ 1131-01-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 3
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 55.48
TPSA ?

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

29.1 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.85
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

1.94
Log Po/w (WLOGP)?

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

2.29
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.

2.44
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

2.84
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.27

Water Solubility

Log S (ESOL):?

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

-2.43
Solubility 0.732 mg/ml ; 0.0037 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.

-2.18
Solubility 1.32 mg/ml ; 0.00668 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

-4.2
Solubility 0.0126 mg/ml ; 0.0000635 mol/l
Class?

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

Moderately 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

 No
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.

-6.13 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

 1.0
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.

0.0 alert
Brenk?

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

1.0 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)

 1.36

Application In Synthesis of [ 1131-01-7 ]

* 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 [ 1131-01-7 ]

[ 1131-01-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 67129-08-2 ]
  • [ 288-13-1 ]
  • [ 1131-01-7 ]
  • 2
  • [ 67129-08-2 ]
  • [ 288-13-1 ]
  • [ 4073-98-7 ]
  • [ 1131-01-7 ]
  • 3
  • [ 108-18-9 ]
  • [ 1131-01-7 ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol; Part B. Synthesis of N-(2,6-dimethylphenyl)-2-piperazinylacetamide (5). To a solution of compound 3 (5 g, 25.2 mmol) in ethanol (100 mL) was added compound 4 (2.1 g, 25.0 mmol) and N,N-diisopropylamine (3.2 g, 25.2 mmol). The reaction mixture was refluxed for 24 h. The mixture was concentrated in vacuo and the residue was purified by column chromatography (10:1 dichloromethane: methanol) to afford compound 5.
  • 4
  • [ 1131-01-7 ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; Part B. Synthesis of N-(2,6-dimethylphenyl)-2-piperazinylacetamide (5). To a solution of compound 3 in 100 mL EtOH (5 g, 25.2 mmol) was added compound 4 (2.1 g, 25.0 mmol) and N,N-diisopropylethylamine (3.2 g, 25.2 mmol). The reaction mixture was refluxed for 24 h. The mixture was concentrated in vacuo and the residue was purified by column chromatography (10:1, DCM:MeOH) to afford compound 5..
With N-ethyl-N,N-diisopropylamine; In ethanol; Part B. Synthesis of N-(2,6-dimethylphenyl)-2-piperazinylacetamide (5). To a solution of compound 3 in 100 mL EtOH (5 g, 25.2 mmol) was added compound 4 (2.1 g, 25.0 mmol) and N,N-diisopropylethylamine (3.2 g, 25.2 mmol). The reaction mixture was refluxed for 24 h. The mixture was concentrated in vacuo and the residue was purified by column chromatography (10:1, DCM:MeOH) to afford compound 5..
  • 5
  • [ 1131-01-7 ]
  • [ 22916-47-8 ]
  • 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate, m.p. 143°-150° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and 2-chloroaceto-2',6'-xylidide.
  • 6
  • [ 110-85-0 ]
  • [ 1131-01-7 ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
77 - 78% In ethanol; at 80℃; for 3.0h;Product distribution / selectivity; Step 3: Preparation of lambdar-(2,6-dimethyl phenvD-l-piperazine acetamide; 2-Chloro-N-(2,6-dimethylphenyl) acetamide (100 g) and piperazine (182 g) was taken in ethanol (300 ml) and the reaction mass was refluxed for 3 hours at 8O0C. The reaction completion was monitored on thin layer chromatography. After reaction completion, the reaction mass was cooled to 25-300C and demineralized water (800 ml) was added. The reaction mass was cooled to 5-100C and stirred for 30 minutes. The reaction mass was filtered through hyflo bed and washed with demineralized water (200 ml). Reaction mass was extracted <n="14"/>with methylene dichloride and organic layer so obtained was washed with sodium hydroxide solution (20 g sodium hydroxide in 340 ml demineralized water). Organic layer was washed again with demineralized water (100 ml) and then with sodium chloride solution. The solvent was distilled out under vacuum and n-hexane (300 ml) was added to the oil obtained and stirred at room temperature for 5 hours. The solid so obtained was filtered and washed with n-hcxane (100 ml) at ambient temperature to afford 96 g of the title compound having purity 99.08 % by high performance liquid chromatography.Yield- 77%; Step 3: Preparation of./V-(2,6-dimethyl phenvD-1-piperazine acetamide; 2-Chloro-N-(2,6-dimethylphenyl) acetamide (125 g) and piperazine (223 g) was taken in ethanol (325 ml) and the reaction mass was refluxed for 3 hours at 800C. The reaction completion was monitored on thin layer chromatography. After reaction completion, the reaction mass was cooled to 25-300C and demineralized water (1.0 /). The reaction mass was cooled to 5-100C and stirred for 30 minutes. The reaction mass was filtered through hyflo bed and washed with demineralized water (250 ml). Reaction mass was extracted with methylene dichloride and organic layer so obtained was washed with sodium hydroxide solution (25 g <n="16"/>sodium hydroxide in 425 ml demineralized water). Organic layer was washed again with demineralized water (125 ml) and then with sodium chloride solution. The solvent was distilled out under vacuum and n-hexane (500 ml) was added to the oil obtained and stirred at room temperature for 5 hours. The solid so obtained was filtered and washed with n-hexane (125 ml) at ambient temperature to afford 123 g of the title compound having purity 98.31 % by high performance liquid chromatography.Yield- 78% -
In methanol; at 25 - 30℃;Reflux; 25 gm of 2-chloro-N-(2,6-dimethyl phenyl) acetamide, 45 gm of piperazine was charged in a flask containing 150 ml of methanol and heated to reflux. The reaction mixture was stirred at reflux for about 4 hours and then cooled to 25-300C. 150 ml of water was charged to the reaction mixture, cooled to 0-5 0C and maintained for 30 minutes. The reaction mixture was filtered through hyflow bed and washed with water (50 ml). The filtrate was extracted with dichloromethane (250 ml) and the organic layer was washed with water (5 X 50 ml). The final organic layer was washed with 10 % aqueous sodium chloride solution (50 ml). The organic layer was concentrated under vacuum at below 45C to remove about 90 % of the solvent. 75 ml of cyclohexane was added to the concentrated organic layer and stirred at room temperature for 2 hours. The solid was filtered and washed with cyclohexane (10 ml) and dried to give 20.5 gm of the title compound. Melting range: 114C - 1500C
In methanol;Reflux;Product distribution / selectivity; 2-chloro-N-(2,6-dimethylphenyl) acetamide (100 g), piperazine (182 g) and methanol (300 mL) are charged into a round-bottom flask and stirred for 5-10 minutes. The mixture is heated to reflux temperature and maintained for 2-3 hours. The mixture is cooled to 25-35C and water (800 mL) is added. The mixture is stirred for 15-30 minutes, then filtered to remove unwanted solid, and the filter is washed with water (200 mL). Dichloromethane (400 mL) is added to the filtrate and the mixture is stirred for 15-30 minutes. The layers are separated and the aqueous layer is extracted with dichloromethane (400 mL). The combined organic layer is washed with a solution of sodium hydroxide (20 g) in water (350 mL) and the solvent is evaporated at 40-450C. 500 mL of n-hexane is added to the residue at 25-35C and the mixture is maintained for 30-45 minutes. The solid is filtered under reduced pressure, washed with n-hexane (100 mL), and dried at 400C, to afford 88.5 of the title compound.Purity by HPLC: 99.61%.
Step 2: Preparation of Piperazine acetamide (II); 100 gm of chloro acetamide (VIII) and 172 gm of anhydrous piperazine was dissolved in 1000 ml of isopropyl alcohol. The reaction mixture was stirred for 1 hour at reflux temperature. The reaction mass was concentrated to get thick slurry and water (1000 ml) was charged to the slurry. 350 ml of 50% aqueous acetic acid solution was added to adjust pH between 5.0-5.50. The reaction mass was extracted with dichloromethane (3 x 500 ml). The aqueous layer was basified with 720 ml of 5N NaOH solution and extracted with dichloromethane (3 x 500 ml). The combined organic layer was washed with 20% brine solution. The organic layer was separated and concentrated under reduced pressure to get oily mass. Cyclohexane (300 ml) was charged to the oily mass. Stirred for 30 minutes at 45- 5O0C. Cooled to 25-3O0C and stirred for 1 hour. The solid was filtered, washed with 100 ml of cyclohexane and dried under reduced pressure to give 105 gm of white solid.
In methanol;Reflux; 2-chloro-N-(2,6-dimethylphenyl) acetamide 3 (100 g), piperazine 4 (182 g) and methanol (300 mL) are charged into a round-bottom flask and stirred for 5-10 minutes. The mixture was heated to reflux temperature and maintained for 2-3 hours. The mixture was cooled to 25-35 C. and water (800 mL) was added. The mixture was stirred for 15-30 minutes, then filtered to remove unwanted solid, and the filter was washed with water (200 mL). Dichloromethane (400 mL) was added to the filtrate and the mixture was stirred for 15-30 minutes. The layers are separated and the aqueous layer was extracted with dichloromethane (400 mL). The combined organic layer was washed with a solution of sodium hydroxide (20 g) in water (350 mL) and the solvent was evaporated at 40-45 C. 500 mL of n-hexane was added to the residue at 25-35 C. and the mixture was maintained for 30-45 minutes. The solid was filtered under reduced pressure, washed with n-hexane (100 mL), and dried at 40 C., to afford 88.5 of the intermediate compound 5.

  • 7
  • [ 110-85-0 ]
  • [ 1131-01-7 ]
  • 2,2'-(piperazine-1,4-diyl)bis(N-(2,6-dimethylphenyl)acetamide) [ No CAS ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In tetrahydrofuran; at 20℃; for 72.0h; 2, 6-DIMETHYLCHLOROACETANILIDE (1. 977 g, 10 mmol) was dissolved in anhydrous THF (10 mL) and finely powdered anhydrous sodium carbonate (1.5 g) was added with stirring followed by piperazine (0.431 g, 5 mmol). Reaction mixture was stirred at room temperature for 3 days. Solid material was filtered off, washed with ethyl acetate, triturated with IN HC1 and filtered. The aqueous filtrate was brought to basic pH by addition of solid KOH and resulting solution was extracted 3 times with dichloromethane. Organic extracts were dried with magnesium sulfate, decanted and evaporated. Residue was subjected to chromatography using dichloromethane/methanol (95: 5) as a solvent system separating compounds A and B.
  • 8
  • [ 1131-01-7 ]
  • [ 57260-71-6 ]
  • [ 5294-61-1 ]
  • 9
  • [ 142-63-2 ]
  • [ 1131-01-7 ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
63% In ethanol; for 3.0h;Reflux; Preparation of N-(2,6-dimethylphenyl)-1-piperazinylacetamide 58.3 g (0.3 mol) of piperazine hexahydrate was dissolved in 230 ml of ethanol and 50.0 g (0.25 mol) of 2-chloro-N-(2,6-dimethylphenyl)-acetamide was subsquently added. The mixture was heated under reflux for 3 h till completion. The reaction product was cooled to room temperature and filtered. The filter was concentrated under reduced pressure and 80 ml of water was added. The mixture was extracted with dichloromethane and the organic layer was concentrated under vacuum at 60 C. to get 39.4 g of N-(2,6-dimethylphenyl)-1-piperazinylacetamide having a yield of 63%. 1HNMR (CDCl3): 2.23?2.27,s, 6H, 2.67,s, 4H, 2.96?2.98,t, 4H, 3.19?3.21,s, 2H, 7.08?7.26,m, 3H, 8.69,s, 1H.
  • 10
  • piperazine monophosphate [ No CAS ]
  • [ 1131-01-7 ]
  • [ 5294-61-1 ]
YieldReaction ConditionsOperation in experiment
In water;Reflux; Added 1000 ml of water to R.B Flask. 109 gms piperazine was added and stirred to dissolve. pH was adjusted to 5.0-5.5 with 0-phosphoric acid. After stirring for 1-2- h at room temperature. Filtered the reaction mass and solid was isolated as piperazine monophosphate monohydrate and charged further to R.B Flask containing 1000 ml water. 100 gms of [(2,6-Dimethylphenyl)-amino carbonyl methyl)chloride (6) was added and heated the reaction mixture at reflux temperature for 7-8 h. Cooled the reaction mixture at 25-30C and adjusted the pH to 5.5-6.0 with dilute sodium hydroxide solution filtered. Filtrate was washed with 100 ml x 2 methylene chloride and further basified with dilute sodium hydroxide solution and extracted with 500 ml x 3 methylene chloride to obtained compound of formula (7).
 

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