HCID 67000209, compound → HCID 59318289, compound

Participants

Reaction Steps

4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidine hydrochloride (RE1) (52.0 g, 143 mmol) was added to a 5% aqueous potassium carbonate solution (350 mL), followed by extraction with toluene (700 mL×3). Combined organic layers were dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine (48.1 g). Next, a solution of 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine (2.00 g, 6.1 mmol), 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate (RE6) (2.01 g, 5.8 mmol) and potassium carbonate (1.66 g, 12 mmol) in acetonitrile (20 mL) was stirred at 70 to 80° C. for 7 hours. After cooling to room temperature, water (100 mL) was added thereto, followed by extraction with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the obtained concentrated residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→chloroform:methanol=20:1) to obtain the title compound (5-1-1) (3.07 g, quantitative).

Provenance & Evidence