O-Methylhydroxylamine hydrochloride → Piperidin-4-one O-methyl-oxime

HRID 734767Notes

Reaction equation

HRID 734767 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.Cl.[CH3:10][O:11][NH2:12]>CO>[CH3:10][O:11][N:12]=[C:5]1[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 30848514-Piperidone hydrochloride

Product 1

HCID 14878799Piperidin-4-one O-methyl-oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.84 g (25.00 mmol) 4-piperdinone hydrochloride and 2.51 g (30.00 mmol) O-methylhydroxylamine hydrochloride in 50 mL of MeOH was stirred for 8 hours at 60° C. and then evaporated down in vacuo. The residue was stirred with saturated aqueous potassium carbonate solution and the aqueous phase was extracted with DCM. The combined organic phases were dried over sodium sulfate, evaporated down in vacuo, and dried. Yield: 2.80 g (87% of theoretical); C6H12N2O (M=128.172); calc.: molpeak (M+H)+: 129; found: molpeak (M+H)+: 129; HPLC-MS: 1.44 minutes (method C).

Workup

  1. customevaporated down in vacuo
  2. stirringThe residue was stirred with saturated aqueous potassium carbonate solution
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated down in vacuo
  6. customdried
  7. custom1.44 minutes (method C)

Sources & evidence

ORD record
ord-786f896e9b824c1aa9c569638d175451
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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