Methanol → HCID 22468680, compound

Participants

Reaction Conditions

Reaction Steps

26 cm3 of aqueous 5N sodium hydroxide and 20 cm3 of methanol were added to a solution of 1.47 g of ethyl 4-[3-(3-chloro-6,7-dimethoxyquinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]piperidine-4-carboxylate in 20 cm3 of dioxane, with stirring and at a temperature in the region of 20° C., and the mixture was then maintained at a temperature of about 70° C. for 21 hours. The reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography under a pressure of 50 kPa of argon, on a column of silica gel (particle size 40-63μ; mass 60 g), eluting with a mixture of dichloromethane/methanol/aqueous ammonia (12/3/0.5 by volume). Fractions 11 to 25 were combined and then concentrated to dryness under the above conditions. 1.03 g of 4-[3-(3-chloro-6,7-dimethoxy-quinolin-4-yl)propyl]-1-[2-(thiophen-2-ylthio)ethyl]-piperidine-4-carboxylic acid was obtained in the form of a white solid melting at 214° C.

Provenance & Evidence