Chloroform → 5-[4-(4-Methylbenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 1649220Notes

Reaction equation

HRID 1649220 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.C(N(CC)CC)C.C(Cl)(Cl)Cl.[CH3:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>O>[CH3:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([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:35])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6212Chloroform3×HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 11630008HCID 11630008, compound

Product 1

HCID 132363395-[4-(4-Methylbenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 2.34 ml of triethylamine were added to 50 ml of chloroform. The mixture was stirred at room temperature while slowly adding dropwise 10 ml of chloroform solution containing 2.3 g of 4-methylbenzoyl chloride. After completion of addition, the reaction mixture was stirred for 30 minutes. After completion of reaction, 100 ml of chloroform and then a large amount of water was added to separate chloroform and the chloroform layer 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 chloroformether to give 1.8 g of 5-[4-(4-methylbenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 239.5°-240° C., colorless powders.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred for 30 minutes
  3. customto separate chloroform
  4. washthe chloroform layer 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 chloroformether

Sources & evidence

ORD record
ord-df8d394e4a35424e9270e2f5321cfc4f
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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