Methyl 1-benzyl-2,4-dioxo-3-piperidinecarboxylate → 1-Benzylpiperidine-2,4-dione

HRID 1815820Notes

Reaction equation

HRID 1815820 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10](C(OC)=O)[C:9]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C(O)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C:9]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 22495601Methyl 1-benzyl-2,4-dioxo-3-piperidinecarboxylate

Product 1

HCID 224955411-Benzylpiperidine-2,4-dioneYield 27.4%

Reagents, catalysts & solvents 1

HCID 971Oxalic AcidSolvent

Procedure

A mixture of 23.4 gm (89.7 mMol) methyl 1-benzyl-2,4-dioxo-3-piperidinecarboxylate in 200 mL 10% aqueous oxalic acid was stirred at reflux for 15 hours. The reaction mixture was cooled to room temperature and the solution extracted with 3×200 mL dichloromethane. The organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure to provide 4.99 gm (27%) of the desired compound.

Workup

  1. temperatureat reflux for 15 hours
  2. extractionthe solution extracted with 3×200 mL dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b56302e6a494defbd6e0c40cbc65ef7
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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