Acetone → 2,2,6,6-Tetramethyl-4-piperidone

HRID 1414087Notes

Reaction equation

HRID 1414087 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])N=1.CC(C)=[O:14]>Cl.C1(NN)C=CC=CC=1.CO>[CH3:10][C:4]1([CH3:11])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2](=[O:14])[CH2:1]1

Participants

5

Reactant 2

HCID 180AcetoneHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 75%

Reagents, catalysts & solvents 2

HCID 60962Phenylhydrazine hydrochlorideCatalystHCID 887MethanolSolvent

Procedure

A flask with attached condenser was charged with 80 g of acetonine, 80 g of acetone, 16 g methanol and 1.6 g N-phenylhydrazine monohydrochloride and the mixture reacted at 50°-55° C. for 18 hours, while stirring. The reaction solution was stripped under reduced pressure, to obtain a light red residue. This residue was distilled in vacuo to obtain 60.4 g of triacetonamine. White crystals were obtained by recrystallization from petroleum ether having the melting point of 34°-36° C. The compound was confirmed to be the objective matter by IR spectrum and gas chromatography.

Workup

  1. customA flask with attached
  2. customthe mixture reacted at 50°-55° C. for 18 hours
  3. customto obtain a light red residue
  4. distillationThis residue was distilled in vacuo

Sources & evidence

ORD record
ord-db6825e056c74d1485fbc90964a0eb00
Source dataset
uspto-grants-1981_02
Patent number
US04252958

Reaction notes

Loading…