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

HRID 557008Notes

Reaction equation

HRID 557008 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]>C(OCC)C>[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

4

Reactant 2

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

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-olYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1-benzyl-4-piperidone (4.9 mL, 26.5 mmol) in anhydrous diethyl ether (50 mL) was cooled to −78° C. and treated with methyllithium (1.4 M, 21 mL, 29 mmol). This mixture was stirred for 2.5 hr at −78° C., then quenched with aqueous brine, and extracted with ethyl acetate (3×100 mL). The combined organics were dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography (CH2Cl2→90:10:1 CH2Cl2/methanol/NH4OH) to yield 4.5 g (83%) of the title compound, ESI-MS m/z: 206 [M+1].

Workup

  1. customquenched with aqueous brine
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel chromatography (CH2Cl2→90:10:1 CH2Cl2/methanol/NH4OH)

Sources & evidence

ORD record
ord-bd25c597926f4a05819ac14f7fe57de2
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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