Sodium Hydroxide → HCID 22470362, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.68 g of ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yloxy)-ethyl]piperidine-4-carboxylate in 7 cm3 of dioxane, 9 cm3 of methanol and 2 cm3 of aqueous 5N sodium hydroxide solution was maintained at a temperature in the region of 60° C. for 20 hours. After cooling to about 20° C., the reaction mass was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was chromatographed under a pressure of 50 kPa of argon, on a column of silica gel (particle size 20-45μ; diameter 2.2 cm; mass 20 g), eluting with a mixture of dichloromethane/methanol (70/30 by volume). The fractions containing the expected product were combined and then concentrated to dryness under the above conditions. The residue obtained was taken up in 5 cm3 of ethyl acetate, stirred for 1 hour at room temperature and then filtered and rinsed with 3 times 3 cm3 of ethyl acetate and then 3 times 3 cm3 of pentane. 0.27 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thiazol-2-yloxy)-ethyl]piperidine-4-carboxylic acid was obtained in the form of a white solid melting at 188° C.

Provenance & Evidence