N,N-Dimethylaniline → HCID 15229768, compound

Participants

Reaction Steps

A solution of 2-hydroxydibenzofuran (5.0 g, 27 mmol) and dimethylaniline (3.4 mL, 27 mmol) in 35 mL of tetrahydrofuran plus 1.5 mL of dioxane was added dropwise under nitrogen to a solution of trichloromethyl chloroformate (1.6 mL, 14 mmol) in 30 mL of tetrahydrofuran at ice bath temperature. After the addition the cooling bath was removed and the stirring continued for approximately 24 hours. The reaction was cooled to ice bath temperature and a solution of 4-phenylbutylamine (4.3 mL, 27 mmol) and pyridine (4.4 mL, 54 mmol) in 30 mL of tetrahydrofuran was added dropwise over 15 minutes. After the addition the reaction was stirred at ice bath temperature for 2 hours. The cooling bath was removed and the stirring continued for approximately 22 hours. The reaction was diluted with ethyl acetate, extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 6.47 g of a yellow solid. Purification of the solid by chromatography on silica gel (230-400 mesh) using hexane-methylene chloride as the eluent gave 1.28 g (13%) of the title compound as a white crystalline solid, mp 113°-114° C.

Provenance & Evidence