Methanol → HCID 18995700, compound

HRID 374761Notes

Reaction equation

HRID 374761 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[ClH:9].[CH3:10][O:11][NH2:12].CO.C(=O)([O-])[O-].[K+].[K+]>O>[ClH:9].[CH3:10][O:11][N:12]=[C:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 740491-Methyl-4-piperidoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 18995700HCID 18995700, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methyl-4-piperidone (5 g, 44.2 mmol) and methoxyamine hydrochloride (3.69 g, 44.2 mmol) were taken into 25 mL of methanol and stirred at room temperature for 2 days. The reaction mixture was evaporated in vacuo to afford a solid residue. The residue was dissolved in water, made basic with solid potassium carbonate, and extracted with dichloromethane (3×100 mL) . The combined extracts were dried over anhydrous sodium sulfate and evaporated to give a clear, yellow liquid that was purified on silica gel, eluting with dichloromethane-methanol (95:5) to afford 2.55 g of the desired product. Treatment with ethereal hydrogen chloride gave the hydrochloride salt, 2.99 g, m.p. 145°-147° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford a solid residue
  3. extractionextracted with dichloromethane (3×100 mL)
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a clear, yellow liquid that
  7. customwas purified on silica gel
  8. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-4d14bebfca6f47f5993c7a7a66479be1
Source dataset
uspto-grants-1996_01
Patent number
US05482938

Reaction notes

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