Trimethylamine → 5-[4-(4-Cyanobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649214Notes

Reaction equation

HRID 1649214 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH2:9][CH2:10][C:11](=[O:17])[NH:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN(C)C.CN(C=O)C.[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)#[N:28]>O>[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[CH2:9][CH2:10][C:11](=[O:17])[NH:12]4)[CH2:2][CH2:3]2)=[O:34])=[CH:31][CH:30]=1)#[N:28]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 6228Dimethylformamide2×HCID 801724-Cyanobenzoyl chlorideHCID 11630008HCID 11630008, compound

Product 1

HCID 132363375-[4-(4-Cyanobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 46.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 2 ml of trimethylamine were added to 40 ml of DMF. The mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.4 g of 4-cyanobenzoyl chloride. After completion of addition, the reaction mixture was stirred at 40° to 50° C. for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 1.9 g of 5-[4-(4-cyanobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 266°-269° C., colorless granules.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at 40° to 50° C. for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with sodium hydrogencarbonate solution and subsequently with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off
  7. customresidual crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-83bcc74758cc45e890c0993bce770db1
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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