Potassium Hydroxide → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

Participants

Reaction Conditions

Reaction Steps

A solution of KOH (12 g, 213.21 mmol) in methanol (100 mL) was added to 5-nitro-1H-indole (15 g, 92.04 mmol) in a 250 mL flask. 1-methylpiperidin-4-one (13.7 g, 120.46 mmol) was then added dropwise with stirring, while cooling the reaction to 20° C. The resulting solution was stirred for 4 hours, while the temperature was maintained at 72° C. The reaction mixture was then cooled to 15° C., and the product was precipitated by the addition of water (100 mL). Filtration, followed by recrystallization of the residue from ethanol afforded 11 g (46%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole as a yellow solid.

Provenance & Evidence