Hydrochloric Acid → HCID 20270200, compound

Participants

Reaction Steps

A suspension of 26.6 g of 3-(4-carboxybutyl)-N-(3-pyridyl)indole and 10.5 g of sulfamide in 90 ml of sulfolane is treated with 11.42 g of thionyl chloride at room temperature under nitrogen. The mixture is heated at 120° until gas evolution ceases and solid p-toluenesulfonic acid monohydrate (1.71 g) is added carefully. After heating an additional 3 hours at 120°, the reaction mixture is cooled, poured onto 200 g of ice and acidified with 130 ml of 1N hydrochloric acid. The aqueous phase is sequentially extracted with ethyl acetate (3×100 ml), made basic with solid sodium bicarbonate and reextracted with ethyl acetate (3×125 ml). The organic extracts are washed with 0.5N sodium hydroxide (5×50 ml), dried over sodium sulfate and evaporated to yield and oil which is chromatographed on 60 g of silica gel to yield 3-(4-cyanobutyl)-N-(3-pyridyl)indole.

Provenance & Evidence