HCID 19031208, compound → HCID 14969526, compound

HRID 1708275Notes

Reaction equation

HRID 1708275 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:12]([C:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][C:22]3=[O:23])[CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24][C:22]3=[O:23])[CH2:19][CH2:20]2)=[O:14])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 19031208HCID 19031208, compound

Product 1

HCID 14969526HCID 14969526, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1-[1-(4-Benzyloxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (4.76 g) is dissolved in methanol (100 ml) and thereto is added 5% palladium-carbon (1 g). The mixture is stirred at room temperature under 1 atm. under hydrogen atmosphere. After the completion of the reaction, the catalyst is filtered off and the filtrate is concentrated. The resultant is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:1) and further recrystallized from n-hexane/ethanol to give 1-[1-(4-hydroxybenzoyl)-4-piperidinyl]-3,4-dihydro carbostyril (2.5 g) as white powder, m.p. 182°-183° C.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated
  4. customThe resultant is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=1:1)
  5. customfurther recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-2b687d1c4e834c4db4cffef94e9b4be3
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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