Isoarecolone → HCID 21284374, compound

A solution of 1-(1,2,3,6-tetrahydro-1-methyl-4pyridinyl)ethanone, O-methyloxime (3 g, 17.8 mmol) in 20 ml dry dichloromethane was cooled to 0° C., treated dropwise with 1-chloroethylchloroformate (2.55 g, 17.8 mmol), and stirred 18 hours at room temperature. The reaction mixture was then concentrated in vacuo to an oil which was heated under reflux one hour in 50 ml of methanol. The methanol was distilled off and the residue was chromatographed over silica gel eluting with 5% methanol in ethyl acetate. The desired fractions were combined, concentrated in vacuo, and treated with methanolic hydrogen chloride to give 1.75 g of 1-(1,2,3,6-tetrahydro-4-pyridinyl)ethanone, O-methyloxime hydrochloride, mp 185°-186° C.

1. concentrationThe reaction mixture was then concentrated in vacuo to an oil which
2. temperaturewas heated
3. temperatureunder reflux one hour in 50 ml of methanol
4. distillationThe methanol was distilled off
5. customthe residue was chromatographed over silica gel eluting with 5% methanol in ethyl acetate
6. concentrationconcentrated in vacuo
7. additiontreated with methanolic hydrogen chloride

ORD record

ord-c20c6739832b4be79317f179702877f9

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04786648