1-Phenyl-4-piperidinone → 1-Phenyl-piperidin-4-one oxime

HRID 37849

Reaction equation

HRID 37849 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][OH:16]>CO>[C:1]1([N:7]2[CH2:12][CH2:11][C:10](=[N:15][OH:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4130091-Phenyl-4-piperidinoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3438331-Phenyl-piperidin-4-one oximeYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-phenyl-piperidin-4-one (180 mg, 1.03 mmol) and hydroxylamine hydrochloride (142 mg, 2.06 mmol) in methanol (10 mL) was heated at reflux for 6 h. The solvent was evaporated and the residue diluted with water. The mixture was extracted with ethyl acetate then the organic phase was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to afford 1-phenyl-piperidin-4-one oxime (0.18 g, 92%) as a liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. customThe solvent was evaporated
  4. additionthe residue diluted with water
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a67ca0e59ef49e293898d43ff28ca5e
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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