Vesnarinone → 1-Acetyl-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 845743

Reaction equation

HRID 845743 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]3)[CH2:12][CH2:11]1)=[O:9].[C:32](Cl)(=[O:34])[CH3:33]>CN(C)C=O>[C:32]([N:22]1[C:23]2[C:18](=[CH:17][C:16]([N:13]3[CH2:12][CH2:11][N:10]([C:8](=[O:9])[C:7]4[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:5]([O:4][CH3:3])[CH:6]=4)[CH2:15][CH2:14]3)=[CH:25][CH:24]=2)[CH2:19][CH2:20][C:21]1=[O:26])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 5663VesnarinoneHCID 6367Acetyl chlorideHCID 24758Sodium hydride

Product 1

HCID 139135291-Acetyl-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 263 mg) was suspended in dimethylformamide (DMF) (30 ml). To the suspension was added 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (2 g) and the mixture was stirred at 70° to 80° C. for 30 minutes. After cooling, to the mixture was added slowly acetyl chloride (0.43 m/g) with stirring and under ice-cooling, and the mixture was stirred at the same temperature for 5 minutes. After completion of reaction, the reaction mixture was poured into ice-water and extracted with chloroform. The chloroform layer was washed successively with water and saturated saline solution and dried over magnesium sulfate. The chloroform extract was evaporated under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:1) and recrystallized from a mixture of dichloromethane and diethyl ether to give 1-acetyl-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (700 mg).

Workup

  1. temperatureAfter cooling, to the mixture
  2. stirringwith stirring and under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred at the same temperature for 5 minutes
  5. customAfter completion of reaction
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed successively with water and saturated saline solution
  8. dry with materialdried over magnesium sulfate
  9. extractionThe chloroform extract
  10. customwas evaporated under reduced pressure
  11. customThe resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol=100:1)
  12. customrecrystallized from a mixture of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-4ea69cdd5e044a10b413f71ff6440150
Source dataset
uspto-grants-1988_07
Patent number
US04760064

Linked notes

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