HCID 14180684, compound → HCID 13913535, compound

HRID 845747Notes

Reaction equation

HRID 845747 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[C:12]([N:14]1[C:24]2[C:19](=[CH:20][C:21]([N:25]3[CH2:30][CH2:29][N:28]([C:31](=[O:42])[C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=4)[CH2:27][CH2:26]3)=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:15]1=[O:16])=[O:13])C1C=CC=CC=1>C(O)C.CN(C=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][CH:45]=1)[C:12]([N:14]1[C:24]2[C:19](=[CH:20][C:21]([N:25]3[CH2:26][CH2:27][N:28]([C:31](=[O:42])[C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=4)[CH2:29][CH2:30]3)=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:15]1=[O:16])=[O:13]

Participants

5

Reactant 1

HCID 14180684HCID 14180684, compound

Product 1

HCID 13913535HCID 13913535, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Benzyloxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (6 g) was dissolved in a mixture of ethanol (100 ml) and DMF (50 ml), and 10% palladium on carbon (1 g) was added thereto. The mixture was hydrogenated at 50° C. After completion 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:ethyl acetate:methanol=100:2) to give 1-(3-hydroxybenzoyl)-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (4.0 g).

Workup

  1. additionwas added
  2. customwas hydrogenated at 50° C
  3. customAfter completion of reaction
  4. filtrationthe catalyst was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe resultant residue was purified by silica-gel column chromatography (eluent:ethyl acetate:methanol=100:2)

Sources & evidence

ORD record
ord-dab0d2b548294a70847db46572cd4a78
Source dataset
uspto-grants-1988_07
Patent number
US04760064

Reaction notes

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