Potassium Iodide → HCID 86758161, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.35 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(2-chloroethyl)piperidine-3-carboxylate dihydrochloride in 20 cm3 of acetonitrile was stirred at a temperature in the region of 20° C. under an inert atmosphere. 1.37 g of potassium carbonate and 0.456 g of potassium iodide were added, followed by 0.367 g of 2-mercaptopyridine and 1 cm3 of methanol. A red suspension was obtained, which suspension was heated at a temperature in the region of 80° C. for 1 hour 30 minutes. After cooling the reaction mass to a temperature in the region of 20° C., the insoluble material was filtered off and washed with acetonitrile. The filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The evaporation residue was purified by chromatography under a nitrogen pressure of 100 kPa on a column of silica gel (particle size 40-63 μm; diameter 3.5 cm; silica height 35 cm), elution was carried out with an ethyl acetate/methanol (95/5 by volume) mixture, and 35-cm3 fractions were collected. Fractions 19 to 40 were combined and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.77 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(pyridin-2-ylthio)ethyl]piperidine-3-carboxylate was obtained in the form of a viscous oil with a red color.

Provenance & Evidence