Potassium Iodide → methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cycloheptylthio)ethyl]piperidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture composed of 3.06 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate, 1.79 g of 2-chloroethyl cycloheptyl sulfide, 5.39 g of potassium carbonate, and 1.29 g of potassium iodide in 75 cm3 of acetonitrile was heated with stirring and under an inert atmosphere at a temperature in the region of 72° C. for 24 hours. After cooling to approximately 20° C., the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μ; diameter 4 cm; mass 150 g), elution was carried out with an ethyl acetate/methanol (95/5 by volume) mixture, and 50-cm3 fractions were collected. The fractions comprising the desired product were combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.6 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cycloheptylthio)ethyl]piperidine-3-carboxylate were obtained in the form of a viscous oil.

Provenance & Evidence