1-Benzyl-4-piperidone → 1-Benzyl-4-methylpiperidin-4-ol

HRID 238286Notes

Reaction equation

HRID 238286 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][Mg]Br.[Cl-].[NH4+]>C1COCC1.CCOCC>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-4-piperidone (26.5 mmol, 5 g) in THF (50 mL) was cooled to −15° C. and a solution of methyl magnesium bromide in ether (3 M, 22 mL) was added. The mixture was stirred for 0.5 hours then allowed to warm to room temperature. Saturated aqueous ammonium chloride (50 mL) was added and the products were extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a pale yellow solid (5.0 g) that was used directly without further purification.

Workup

  1. extractionthe products were extracted into ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum

Sources & evidence

ORD record
ord-7c4bdb5ed68c4c7db9fbbf0069da3577
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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