Methyl iodide → 1-Benzyl-3,3-dimethylpiperidin-4-one

HRID 917091Notes

Reaction equation

HRID 917091 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16]C(C)([O-])C.[K+].CI>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-Benzyl-3-methyl-piperidin-4-one (2.03 g, 10 mmol) in THF (10 mL) was added potassium t-Butoxide (1.1 g, 10 mmol) and methyl iodide (0.62 mL, 10 mmol). The solution was then stirred at room temperature for about 72 hours. The reaction was quenched with brine and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, then purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

Workup

  1. customThe reaction was quenched with brine
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-01ebc23b1dea4cd3a00c7d0779f7928b
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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