O-methylhydroxylammonium chloride → Piperidin-4-one O-methyl-oxime

HRID 622446Notes

Reaction equation

HRID 622446 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH3:10][O:11][NH3+:12].[Cl-]>N1C=CC=CC=1>[CH3:10][O:11][N:12]=[C:6]1[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 2723901Piperonylamine

Product 1

HCID 14878799Piperidin-4-one O-methyl-oximeYield 89.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

53 ml of anhydrous pyridine were added to a mixture of 3.34 g of 4-piperidone hydrochloride monohydrate and 2.0 g of o-methylhydroxylamine hydrochloride, and the mixture was kept stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off, and the crystalline residue was washed with ethyl acetate and collected by filtration. The crystals were washed with saturated aqueous sodium bicarbonate solution until basic and then extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was stripped off, giving 2.5 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. washthe crystalline residue was washed with ethyl acetate
  4. filtrationcollected by filtration
  5. washThe crystals were washed with saturated aqueous sodium bicarbonate solution until basic
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-d45dbc8cbcdb4c669dc20c16709758d6
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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