HCID 19030719, compound → HCID 14969540, compound

HRID 266821Notes

Reaction equation

HRID 266821 reaction equation
[CH:1]([C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)=[CH2:2]>C(O)C.[C].[Pd]>[CH2:1]([C:3]1[CH:27]=[CH:26][C:6]([C:7]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18][C:16]3=[O:17])[CH2:13][CH2:14]2)=[O:8])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 19030719HCID 19030719, compound

Product 1

HCID 14969540HCID 14969540, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-[1-(4-Vinylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.6 g) is dissolved in ethanol (10 ml) and thereto is added 10% palladium-carbon (0.1 g) and the mixture is stirred under hydrogen atmosphere. After the reaction, the catalyst is removed by filtration and the filtrate is concentrated. The resultant is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) and recrystallized from n-hexane/ethanol to give 1-[1-(4-ethylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.5 g) as white powder, m.p.: 133°-134° C.

Workup

  1. customAfter the reaction
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe resultant is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)
  5. customrecrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-0207ef1df40e41109ef5566a337f685c
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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