Methyl iodide → 1-Benzyl-3,3-dimethylpiperidine-2,4-dione

HRID 1815821Notes

Reaction equation

HRID 1815821 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].I[CH3:23]>CS(C)=O.C(OCC)(=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:23])([CH3:9])[C:16]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224955411-Benzylpiperidine-2,4-dione

Product 1

HCID 224956821-Benzyl-3,3-dimethylpiperidine-2,4-dioneYield 37.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.44 gm (7.1 mMol) 1-benzyl-2,4-dioxopiperidine, 4.0 gm (28.9 mMol) potassium carbonate, and 1.5 mL (24.1 mMol) iodomethane in 14 mL dimethylsulfoxide was stirred for 24 hours. The reaction mixture was diluted with ethyl acetate and water. The phases were separated and the organic phases was washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with hexane containing 35% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.61 gm (37%) of the desired compound.

Workup

  1. customThe phases were separated
  2. washthe organic phases was washed sequentially with water and saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluting with hexane containing 35% ethyl acetate
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08f78e16cae14d62b59c4b140d0f3eee
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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