Water → 1-Benzyl-4-methylpiperidin-4-ol

HRID 322156Notes

Reaction equation

HRID 322156 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][Li].O>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

5

Reactant 3

HCID 962WaterHCID 192201-Benzyl-4-piperidoneHCID 178418348HCID 178418348, compound

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-olYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1-benzyl-4-piperidone (5.00 mL, 27.0 mmol, 1.00 equiv, Aldrich) in anhydrous ether at −78° C. under argon was added methyllithium (1.4M in Et2O, 54.0 mL, 53.9 mmol, 2.00 equiv). Stirring was continued at −78° C. for 1.5 hours. Ether (200 mL) and water (40 mL) were added, and the two phases were separated. The aqueous solution was extracted with Et2O (3×50 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc to EtOAc-MeOH 9:1) to give 4.81 g (87%) of colorless oil, which was characterized spectroscopically.

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous solution was extracted with Et2O (3×50 mL)
  3. dry with materialThe combined organic solutions were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc to EtOAc-MeOH 9:1)

Sources & evidence

ORD record
ord-7e1141f9d3c14360b2134d487c5871c7
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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