1-Benzyl-3,3-dimethylpiperidin-4-one → 3,3-Dimethylpiperidin-4-one

HRID 746877Notes

Reaction equation

HRID 746877 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:15][C:10]1([CH3:16])[C:11](=[O:14])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 97944131-Benzyl-3,3-dimethylpiperidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 222788373,3-Dimethylpiperidin-4-oneYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-3,3-dimethyl-4-piperidone 275 g (1.26 mol), was dissolved in 1.0 L. methanol. The solution was transferred to a Parr reactor after adding 10% palladium on carbon (25 g). The reaction mixture was stirred under 300 psi hydrogen pressure at 60° C. until chromatography showed complete conversion. The reaction mixture was filtered and the residue washed with methanol (200 ml). The filtrate was concentrated to dryness to afford 3,3-dimethyl-4-piperidone (158 g) which was used as such for the preparation of either 4-benzyloxycarbonylamino-3,3-dimethylpiperidine or 4-t-butyloxycarbonylamino-3,3-dimethylpiperidine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with methanol (200 ml)
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5a4018544c254ac7bcc8fabb0b349b8a
Source dataset
uspto-grants-2008_07
Patent number
US07393957B2

Reaction notes

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