Hydrochloric Acid → HCID 70176831, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.3 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)ethyl]piperidine-3-acetate in 8 cm3 of dioxane in the presence of 0.5 cm3 of 5N aqueous sodium hydroxide solution was heated with stirring at a temperature in the region of 60° C. for 20 hours. After cooling to a temperature in the region of 20° C., the reaction mixture was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. A foam with a yellow color was obtained, which product was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 1.6 cm; silica volume 40 cm3), elution was carried out with a chloroform/methanol/28% aqueous ammonia (12/3/0.5 by volume) mixture, and first a fraction of 125 cm3 and then approximately 10-cm3 fractions were collected. Fractions 3 to 7 were combined and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.27 g of a lacquer was obtained, which product was taken up in 5 cm3 of dioxane, 11 cm3 of 0.1N aqueous hydrochloric acid and 14 cm3 of distilled water. The dioxane was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the residual solution was lyophilized. 0.29 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclohexylthio)-ethyl]piperidine-3-acetic acid dihydrochloride was obtained in the form of a lyophilizate with a white color.

Provenance & Evidence