Water → Batelapine

HRID 1982138Notes

Reaction equation

HRID 1982138 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=[C:6](SC#N)[N:5]2[N:18]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:1][C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=[C:6]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[N:5]2[N:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 233173522-methyl-5-cyanothio-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine

Product 1

HCID 60717Batelapine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 6.25 g of 2-methyl-5-cyanothio-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine in 7.3 ml of hexamethylphosphoramide is added dropwise, at 0°, 4.94 g of N-methylpiperazine over a period of 5 minutes. The mixture is stirred at room temperature for 4 hours, poured into water and extracted with ethyl acetate. The organic extracts are washed with water, dried over magnesium sulfate and evaporated to dryness to give 2-methyl-5-(4-methyl-1-piperazinyl)-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine, m.p. 185°-187°. This material is treated with an equivalent amount of maleic acid to give 2-methyl-5-(4-methyl-1-piperazinyl)-11H-1,2,4-triazolo[2,3-c][1,3]benzodiazepine monomaleate of example 1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts are washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-82869b2cd3604438aa10bb99d84a35a2
Source dataset
uspto-grants-1986_06
Patent number
US04595535

Reaction notes

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