1-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril → 1-[1-(4-Hydroxymethylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril

HRID 483516Notes

Reaction equation

HRID 483516 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)=[O:2].B.[Na]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][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:26][CH:27]=1

Participants

4

Reactant 2

HCID 190308281-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyrilHCID 178418435HCID 178418435, compound

Product 1

HCID 190311061-[1-(4-Hydroxymethylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyrilYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (500 mg) is dissolved in methanol (10 ml) and thereto is added sodium boron hydride (63 mg) under ice cooling and the mixture is stirred for 2 hours. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=2:1) and recrystallized from n-hexane/ethanol to give 1-[1-(4-hydroxymethylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (390 mg) as white powder, m.p.: 138°-139° C.

Workup

  1. concentrationThe solvent is concentrated
  2. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=2:1)
  3. customrecrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-513a93df7e4c405b8e12abd0dbb6f90b
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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