Hydrochloric Acid → 5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole

Participants

Reaction Steps

44 g of the hydrochloride of 4-piperidone monohydrate were added at 100° C. to a solution of 12.6 g of 5-methoxy-indole in 240 ml of acetic acid and the mixture was held at 100° C. for 30 minutes and was then cooled and poured into ice water containing 400 ml of concentrated ammonium hydroxide solution. The mixture was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride solution, was dried over magnesium sulfate and was evaporated to dryness to obtain 20 g of raw product. The latter was chromatographed over silica gel and elution with a 7-2-1 chloroform-methanol-triethylamine mixture yielded 5.26 g of 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in the form of a resin.

Provenance & Evidence