Water → 6,6-Dimethylpiperidine-2,4-dione

HRID 1196416Notes

Reaction equation

HRID 1196416 reaction equation
[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[CH:5](C(OC)=O)[C:4](=[O:13])[CH2:3]1.O>Cl.C(#N)C>[CH3:1][C:2]1([CH3:14])[NH:7][C:6](=[O:8])[CH2:5][C:4](=[O:13])[CH2:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 19898238Methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylate

Product 1

HCID 126955936,6-Dimethylpiperidine-2,4-dioneYield 39.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 6,6-dimethylpiperidine-2,4-dione-3-carboxylate (26.3 g), water (30 ml) and concentrated hydrochloric acid (3 drops) in acetonitrile (300 ml) was heated at reflux for 4 hours. The cooled solution was evaporated under reduced pressure and the residue recrystallised from water (50 ml) to give 6,6-dimethylpiperidine-2,4-dione (7.3 g), mp 183°-184° C., as a cream crystalline solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe cooled solution was evaporated under reduced pressure
  4. customthe residue recrystallised from water (50 ml)

Sources & evidence

ORD record
ord-c5bf290599e847c09e4d88651cd7be55
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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