Hydroxyamine hydrochloride → 2,6-Dimethyl-1-(phenylmethyl)-4-piperidinone oxime

HRID 1492730Notes

Reaction equation

HRID 1492730 reaction equation
[CH2:1]([N:8]1[CH:13]([CH3:14])[CH2:12][C:11](=O)[CH2:10][CH:9]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].C([O-])(=O)C.[Na+]>CO.O>[CH2:1]([N:8]1[CH:13]([CH3:14])[CH2:12][C:11](=[N:18][OH:19])[CH2:10][CH:9]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 15714117(2S,6S)-1-benzyl-2,6-dimethylpiperidin-4-one

Product 1

HCID 157141182,6-Dimethyl-1-(phenylmethyl)-4-piperidinone oximeYield 48.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

10 g of 1-benzyl-2,6-dimethyl-4-piperidone (prepared from benzylamine and ethyl crotonate in analogy to Bull. Chem. Soc. Japan 31 (1958) 418) are dissolved in 60 ml of methanol and this solution is added dropwise to a solution of 3.8 g of hydroxylamine hydrochloride and 4.5 g of sodium acetate in 150 ml of water. The mixture is stirred at 60° C. for 2 h and cooled to 0° C., and the oxime which has separated out is filtered off with suction. Drying results in 5.2 g of the title compound.

Workup

  1. temperaturecooled to 0° C.
  2. customthe oxime which has separated out
  3. filtrationis filtered off with suction
  4. customDrying

Sources & evidence

ORD record
ord-990a33963fb14dfa80cee02850273089
Source dataset
uspto-grants-1994_12
Patent number
US05374731

Reaction notes

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