Acetone → HCID 20254912, compound

HRID 638003Notes

Reaction equation

HRID 638003 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:31][CH3:32])=[C:9]([CH:30]=1)[C:10]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=[O:11])#[N:4].CC(C)=O>C(O)C>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:31][CH3:32])=[C:9]([CH:30]=1)[C:10]([NH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][C:18](=[C:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[OH:29])[CH2:17][CH2:16]1)=[O:11])#[N:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 3050428PrideperoneHCID 4311764Sodium borohydride

Product 1

HCID 20254912HCID 20254912, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.38 g (0.01 mol) of sodium borohydride are added, while stirring, to a suspension of 4.1 g (0.01 mol) of 5-cyano-N-[2-[4-(p-fluorobenzoyl)-piperidinyl]ethyl]-2-methoxybenzamide in 50 ml of ethanol and the whole is stirred for 1 hour at room temperature. There is added to the resulting clear solution 1 ml of acetone and the whole is then concentrated in a water-jet vacuum. The residue is taken up in methylene chloride and water, the layers are separated in a separating funnel and, after being dried over magnesium sulphate, the organic phase is concentrated by evaporation. 5-Cyano-N-[2-[4-[(4-fluorophenyl)hydroxymethylene]-piperidinyl]-ethyl]-2-methoxybenzamide of melting point 135°-137° is obtained as residue.

Workup

  1. concentrationthe whole is then concentrated in a water-jet vacuum
  2. customwater, the layers are separated in a separating funnel
  3. dry with materialafter being dried over magnesium sulphate
  4. concentrationthe organic phase is concentrated by evaporation

Sources & evidence

ORD record
ord-4951b98718c7408589b4833f8edfb304
Source dataset
uspto-grants-1985_12
Patent number
US04559349

Reaction notes

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