Pyridine → HCID 22340289, compound

Participants

Reaction Steps

To a solution of the 2-(1-pyrrolidinylmethyl)-6-quinolinylamine (500 mg, 2.2 mmol) obtained in Reference Example 9 and pyridine (0.356 ml, 4.4 mmol) in tetrahydrofuran (11 ml) was added 4-nitrophenyl chloroformate (488 mg, 2.42 mmol) under ice-cooling. After stirred for 30 minutes, the reaction solution was concentrated, and dimethyl sulfoxide (11 ml) was added to the residue. 4-(4-Fluorophenyl)piperidine hydrochloride (569 mg, 2.64 mmol) and a 4N aqueous sodium hydroxide solution (0.66 ml) were added thereto at room temperature while stirring, and the mixture was stirred for 2 hours. Ethyl acetate and water were added, the mixture was extracted, the organic layer was washed with water, and concentrated, and the residue was purified by alumina column chromatography (developing solvent: ethyl acetate) to obtain the titled compound (612 mg) as a colorless powder from ethyl acetate-diisopropyl ether.

Provenance & Evidence