1-Benzyl-4-piperidone → 3-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-5-bromo-1H-indole

Participants

Reaction Steps

Freshly distilled 1-Benzyl-4-piperidone (11.7 g) was added to a stirred solution of 5-bromoindole (11.0 g) in 2M potassium hydroxide in methanol (81ml). The mixture was stirred at reflux for 8 h and then allowed to cool to 25° over 8 h. The solid was collected by filtration, washed with a mixture of methanol:water (2:1, 2×15 ml) and dried in vacuo at 50° for 18 h to give the title compound as a crystalline solid (18.6 g) m.p. 173°-175° (decomp).

Provenance & Evidence