Thionyl Chloride → HCID 131723270, compound

Participants

Reaction Conditions

Reaction Steps

0.46 cm3 of thionyl chloride was added dropwise to a solution of 1 g of methyl (3R,4R)-1-(3-phenylpropyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)-propyl]piperidine-3-carboxylate in 15 cm3 of chloroform while maintaining the temperature at 0° C. The reaction mixture was allowed to return to a temperature in the region of 20° C. with stirring over 2 hours. The reaction mixture was subsequently concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. The residue was dissolved in 30 cm3 of distilled water and the aqueous phase was washed with 15 cm3 of dichloromethane, then basified to pH 9 with solid potassium carbonate and, finally, extracted with 3 times 20 cm3 of dichloromethane. The organic phases were combined, washed with 2 times 20 cm3 of distilled water, and dried over magnesium sulfate. After filtering and then concentrating under reduced pressure (5 kPa) at a temperature in the region of 45° C., 1.16 g of methyl (3R,4R)-1-(3-phenylpropyl)-4-[3-(R,S)-chloro-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate were obtained in the form of a brown oil.

Provenance & Evidence