4-[p-Chlorobenzoyl]-1-methylpiperidine → alpha-[4-Chlorophenyl]-1-methyl-4-piperidinemethanol

HRID 1992704Notes

Reaction equation

HRID 1992704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2426804-[p-Chlorobenzoyl]-1-methylpiperidineHCID 4311764Sodium borohydride

Product 1

HCID 541856alpha-[4-Chlorophenyl]-1-methyl-4-piperidinemethanolYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-chlorophenyl 1-methylpiperidin-4-yl methanone 1.19 g (5 mmol) in 30 ml methanol was added in small portions sodium borohydride 0.378 g (10 mmol). The reaction mixture was stirred at room temperature for two hours, concentrated, added water and extracted with methylene chloride 2×50 ml. The combined organic solution was dried over sodium sulfate and concentrated to give 1.2 g of desired product in 98% yield.

Workup

  1. concentrationconcentrated
  2. additionadded water
  3. extractionextracted with methylene chloride 2×50 ml
  4. dry with materialThe combined organic solution was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-104bea1ebc3d424fb73fbd98e12557a3
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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