Hydrochloric Acid → 4-Piperidinone O-methyloxime hydrochloride

4-Piperidinone hydrochloride monohydrate (5 g, 32.5 mmol), methoxyamine hydrochloride (4.18 g, 50 mmol) and potassium carbonate (13.82 g, 100 mmol) were taken into 100 mL of ethanol and stirred at room temperature for 16 hours. The reaction mixture was filtered and the filtrate evaporated to afford a white solid. The crude solid 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 in vacuo to afford a clear, colorless liquid. It was converted to its hydrochloride salt by treating with ethereal hydrogen chloride to give 233 g, m.p. 140°-141° C. C6H12N2O·HCl: Calc.: C, 43.77; H, 7.96; N, 17.02. Found: C, 43.78; H, 7.96; N, 17.08.

1. filtrationThe reaction mixture was filtered
2. customthe filtrate evaporated
3. customto afford a white solid
4. extractionextracted with dichloromethane (3×100 mL)
5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
6. customevaporated in vacuo
7. customto afford a clear, colorless liquid
8. customto give 233 g, m.p. 140°-141° C

ORD record

ord-73447badc9bd48a7b64661d66665e8e6

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05306718