Indole → 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

KOH (8.19 g, 146 mmole), indole (3.87 g, 33 mmole) and piperidine-4-one hydrochloride (10.22 g, 85.7 mmole) were suspended in methanol (50 ml) and heated for 8 hours at 65° C. under argon. Water (50 ml) was added dropwise at RT to the mixture over a period of 40 minutes. The solid thereby formed was filtered off, washed with water (3×20 ml) and recrystallised from methanol (20 ml). 3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole was obtained in a yield of 4.26 g (71%) as a yellow solid with an m.p. of 172°-174° C.

Provenance & Evidence