反应详情

A solution of 1-chloro-4-(4-indolyloxy)butane (prepared from 4-hydroxy-1H-indole and 1-bromo-4-chlorobutane), 4-(2-naphthyl)piperidine and 3 equivalents of potassium carbonate in acetonitrile was heated at reflux for 12 h. The mixture was cooled and diluted with ethyl acetate, and the organic layer was separated and washed with brine. The crude residue was purified by silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient eluent). The resulting free base was dissolved in ethyl acetate and precipitated with one equivalent of oxalic acid in ethyl acetate, to give the title compound in 48% overall yield as a tan solid. mp. 113°-115° C. FDMS m/e=398 (M+ of free base).

1. temperatureat reflux for 12 h
2. temperatureThe mixture was cooled
3. customthe organic layer was separated
4. washwashed with brine
5. customThe crude residue was purified by silica gel chromatography (dichloromethane/5% methanol in dichloromethane gradient eluent)
6. dissolutionThe resulting free base was dissolved in ethyl acetate