Water → 2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propylthio]-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

HRID 839290Notes

Reaction equation

HRID 839290 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.[H-].[Na+].Cl.Cl[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[O:40][CH3:41])[CH2:30][CH2:29]1.O>CN(C)C=O>[CH3:41][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[N:31]1[CH2:30][CH2:29][N:28]([CH2:27][CH2:26][CH2:25][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)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8267037-chloro 5-(2-chlorophenyl)-1,3-dihydro-2H-(1,4)-benzodiazepine-2-thioneHCID 27578901-(3-Chloropropyl)-4-(2-methoxyphenyl)-piperazine hydrochloride

Product 1

HCID 203240972-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propylthio]-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
30 °C

Procedure

To a solution of 11.5 g of 1,3-dihydro-5-(2-chlorophenyl)-7-chloro-2H-1,4-benzodiazepine-2-thione in 100 ml of anhydrous dimethylformamide is added under ice cooling with stirring 2.1 g of sodium hydride (50% oily suspension), and the resulting mixture is stirred at 30° C. for 1 hour. To the mixture is added dropwise a solution of 12.5 g of 1-chloro-3-[4-(2-methoxyphenyl)-1-piperazinyl]propane hydrochloride in 50 ml of dimethylformamide over a period of 15 minutes, and the resulting mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into iced 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-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propylthio]-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 isopropyl alcohol to obtain 10.5 g of 2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propylthio]-5-(2-chlorophenyl)-7-chloro-3H-1,4-benzodiazepine fumarate, m.p. 189°-191° C.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-99994dceea0b4f4b90563f9504f8724e
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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