Pyridine → HCID 21939957, compound

Participants

Reaction Steps

Pyridine(9.95 ml, 123 mmol) and 4-nitrophenyl chloroformate (12.4 g, 61.5 mmol) was added to a tetrahydrofuran(300 ml)solution of 6-amino-3,4-dihydro-1(2H)-naphthalenone(9.92 g, 61.5 mmol)obtained in Reference Example 96, which was stirred at room temperature for 3 hours. The solvent was distilled out under reduced pressure. 1N Hydrochloric acid was added to the residue to powder, which was washed with ethanol. 4N Aqueous sodium hydroxide solution was added to a dimethylsulfoxide (33 ml)solution of the resulting 4-nitrophenyl-5-oxo-5,6,7,8-tetrahydro-2-naphthalenylcarbamate (2.20 g, 6.74 mmol) and 4-(4-fluorophenyl)piperidine hydrochloride (1.60 g, 7.42 mmol), which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with 1N hydrochloric acid, aqueous potassium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resulting residue was purified by alumina B column chromatography (development solvent ethyl acetate), and powdered with isopropyl ether and hexane, to give the titled compound (1.89 g).

Provenance & Evidence