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

HRID 1649235

Reaction equation

HRID 1649235 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:24])[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)=[O:7].[H-].[Na+].CN(C=O)C.[CH2:37](Cl)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O>[OH2:2].[CH2:37]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:13][CH2:12]3)=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:24])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[CH2:37]([N:20]1[C:21]2[C:16](=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:13][CH2:12]3)=[CH:23][CH:22]=2)[CH2:17][CH2:18][C:19]1=[O:24])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 5663VesnarinoneHCID 6228Dimethylformamide2×HCID 7503Benzyl ChlorideHCID 24758Sodium hydride

Product 1

HCID 887392701-Benzyl-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril hemihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (500 mg) and 70 mg of 60% oily sodium hydride were mixed with 5 ml of DMF and stirred at room temperature for 1 hour. Then, to the mixture was added dropwise 3 ml of DMF solution containing 0.17 ml of benzylchloride. After stirring for 4 hours at room temperature, the reaction mixture was poured into a large amount of water and organic substances were extracted with chloroform. The chloroform layer was washed with water and dehydrated. Chloroform was distilled off and the residue was recrystallized from ethanol to give 150 mg of 1-benzyl-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril hemihydrate, m.p. 131.5°-132.5° C., yellow powders. Elemental Analysis for

Workup

  1. stirringAfter stirring for 4 hours at room temperature
  2. extractionwere extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. distillationChloroform was distilled off
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9f8f5f37da7c44aab41dab4ec74ca058
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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