Methanol → 2-(2-piperidinoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

HRID 839287Notes

Reaction equation

HRID 839287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:20])[CH2:10][N:9]=1.[OH-].[Na+].CO.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O>[N:29]1([CH2:28][CH2:27][S:20][C:11]2[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=3[N:12]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thione

Product 1

HCID 129470432-(2-piperidinoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 9.6 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 40 ml of a 10% aqueous sodium hydroxide solution and 40 ml of methanol is added dropwise a solution of 5.5 g of 1-chloro-2-piperidinoethane hydrochloride in 20 ml of water over a period of 15 minutes, and the resulting mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate and, thereafter, the solvent is distilled off under reduced pressure to obtain an oily 2-(2-piperidinoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine. The oily product thus obtained is treated, according to usual procedure, with fumaric acid and recrystallized from 99% ethanol to obtain 10.5 g of 2-(2-piperidinoethylthio)-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate, m.p. 196°-198° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-359f316f7dcc41bf98619b8c778bde4b
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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