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

HRID 1257621Notes

Reaction equation

HRID 1257621 reaction equation
COC([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=[O:19])=O>CC#N.O>[CH2:12]([N:7]1[CH2:8][CH2:9][C:10](=[O:11])[CH2:5][C:6]1=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

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

Product 1

HCID 224955411-Benzylpiperidine-2,4-dioneYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-benzyl-2,4-dioxo-piperidine-3-carboxylic acid methyl ester (2.09 g, 8.0 mmol) in MeCN (250 mL) and water (20 mL) was heated at reflux for 76 hours. The cooled reaction mixture was concentrated under vacuum to afford 1.60 g (98%) of 1-benzyl-piperidine-2,4-dione as a yellow oil. 1H NMR (400 MHz, CDCl3) δ: 7.36-7.24 (m, 5H), 4.69 (s, 2H), 3.48 (t, 2H), 3.43 (s, 2H), 2.54 (t, 2H).

Workup

  1. temperatureat reflux for 76 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-deb45b2c28a142a6a082194aea0f5a69
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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