Benzene → HCID 20320085, compound

Participants

Reaction Steps

A mixture of 12.5 g of 4-(1-methyl-[1H]-indol-3-yl)-piperidine hydrochloride, 10.7 g of 2,3-dihydro-2-oxiranyl-1,4-benzodioxin, 0.1 g of hydroquinone, 120 ml of benzene and 20 ml of methanol was refluxed with stirring under nitrogen for 2 hours and was then cooled and poured into 200 ml of ether to effect crystallization. The mixture was treated with 100 ml of aqueous 5% sodium bicarbonate solution and the organic phase was decanted. The aqueous phase was extracted with methylene chloride and the combined organic phases were washed with water until the wash water was neutral, dried, decolorized with activated carbon and evaporated to dryness. The 20 g of brown oil residue was chromatographed over silica gel and was eluted with a 95-5 methylene chloride-methanol mixture. Evaporation of the eluates was followed by crystallization of the residue from ethanol to obtain 8.6 g of α-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(1-methyl-[1H]-indol-3-yl)-1-piperidine-ethanol after a second crystallization from ethanol in the form of a white solid melting at 155° C.

Provenance & Evidence