4-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic Acid → HCID 19753218, compound

Participants

Reaction Conditions

Reaction Steps

To 2.0 g (5.14 mmol) of 4-(4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidinyl)butanoic acid dissolved in 20 ml of dichloromethane was added 1.27 g (6.17 mmol) of dicyclohexylcarbodiimide, and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture was added 1.54 g (6.18 mmol) of 8-amino-6-methoxy-2-methoxycarbonylchromone, and the mixture was further stirred at 0° C. for 3 hours. The reaction mixture was allowed to stand at room temperature overnight and then concentrated under reduced pressure. To the residue was added ethyl acetate, and the insolubles were filtered off. The filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography using a mixed solvent of chloroform and methanol in a volume ratio of 20:1 as an eluent to obtain 0.50 g (yield: 17%) of 1-(3-[N-(6-methoxy-2-methoxycarbonylchromon-8-yl)carbamoyl]propyl)-4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine as a brown foamy product.

Provenance & Evidence