6-[1-Oxo-4-(4-phenylpiperazinyl)-butyl]-3,4-dihydrocarbostyril → 6-[1-Hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril

HRID 2291178Notes

Reaction equation

HRID 2291178 reaction equation
[O:1]=[C:2]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[H][H]>O.[Pd]>[OH:1][CH:2]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 30670756-[1-Oxo-4-(4-phenylpiperazinyl)-butyl]-3,4-dihydrocarbostyrilHCID 178418361HCID 178418361, compound

Product 1

HCID 128335176-[1-Hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2.0 Grams of 6-[1-oxo-4-(4-phenylpiperazinyl)-butyl]-3,4-dihydrocarbostyril and 0.5 g of palladium black were dispersed in 80 ml of water and stirred at a room temperature under 2 atmospheric pressure of hydrogen gas for 5 hours. The reaction mixture was filtered for removing the palladium black and the mother liquor was concentrated under a reduced pressure and the residue thus obtained was crystallized from acetone and a small amount of ethanol. The crude crystals thus obtained were collected by filtration and recrystallized from isopropanol to obtain 1.5 g of 6-[1-hydroxy-4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydrocarbostyril in colorless needle like crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customfor removing the palladium black
  3. concentrationthe mother liquor was concentrated under a reduced pressure
  4. customthe residue thus obtained
  5. customwas crystallized from acetone
  6. customThe crude crystals thus obtained
  7. filtrationwere collected by filtration
  8. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-605964c89e504a4bb8a692b57ac3a42f
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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