Sodium Hydroxide → HCID 21347699, compound

Participants

Reaction Conditions

Reaction Steps

0.9 cm3 of 5N aqueous sodium hydroxide was added to a solution of 0.58 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenyl)propyl]piperidine-3-carboxylate in 21 cm3 of methanol and then the mixture was heated at a temperature in the region of 60° C. for 20 hours, on conclusion of which 0.2 cm3 of 5N aqueous sodium hydroxide was added. Heating was subsequently continued for 3 hours. After cooling to a temperature in the region of 25° C., the solution was evaporated under reduced pressure (1 kPa) at a temperature in the region of 40° C. The residue was taken up in 30 cm3 of water and then treated with 7.8 cm3 of 1N hydrochloric acid. After extracting the aqueous phase with 5 times 10 cm3 of dichloromethane, the aqueous phase was evaporated to dryness under reduced pressure (1 kPa) at a temperature in the region of 60° C. The residue obtained was triturated in 10 cm3 of a dichloromethane/methanol (90/10 by volume) mixture. The insoluble material was filtered off and then the cake was washed with 2 times 5 cm3 of the same mixture. The filtrate was dried over sodium sulfate and then evaporated to dryness under reduced pressure (1 kPa) at a temperature in the region of 40° C. 0.46 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(3-fluorophenyl)propyl]piperidine-3-carboxylic acid was obtained in the form of a foamy solid with a pale yellow color which melts at approximately 206° C.

Provenance & Evidence