Ethanol → 1-(4-Aminobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril

HRID 845746Notes

Reaction equation

HRID 845746 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([C:8]([N:10]2[C:20]3[C:15](=[CH:16][C:17]([N:21]4[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=5)[CH2:23][CH2:22]4)=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:11]2=[O:12])=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(O)C>[Pd].CN(C=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[C:20]3[C:15](=[CH:16][C:17]([N:21]4[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]5[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=5)[CH2:25][CH2:26]4)=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:11]2=[O:12])=[O:9])=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 141806831-(4-Nitrobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]3,4-dihydrocarbostyril

Product 1

HCID 139135341-(4-Aminobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyrilYield 31.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(4-nitrobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (1.5 g) and ethanol (30 ml) were added DMF (5 ml) and 10% palladium on carbon (300 mg). The mixture was hydrogenated at 50° to 60° C. After competion of reaction, the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol= 100:2) and recrystallized from ethanol to give 1-(4-aminobenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (0.45 g).

Workup

  1. customwas hydrogenated at 50° to 60° C
  2. customAfter competion of reaction
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe resultant residue was purified by silica-gel column chromatography (eluent:dichloromethane:methanol= 100:2)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-72a9815b08e14f788ca011a85d702919
Source dataset
uspto-grants-1988_07
Patent number
US04760064

Reaction notes

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