4-Cyanobenzenesulfonyl chloride → HCID 21221824, compound

Participants

Reaction Steps

A solution of 2-(N,N-dipropylamino)-5,6-bis(aminomethyl)indane 52 (0.276 g, 1.00 mmol) in pyridine (4.0 ml) was cooled in ice, and 4-cyanobenzenesulfonyl chloride (0.61 g, 3.0 mmol) was added. The mixture was stirred at room temperature for 4 hours. The mixture was diluted with 10% sodium carbonate solution and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a dark oil. Purification by flash chromatography (230-400 mesh silica gel, 60-80% ethyl acetate/hexane) gave the title compound (54) as an oil. The compound was dissolved in ethyl acetate and excess ethereal hydrochloric acid was added. The mixture was diluted with diethylether and filtered. The precipitate was washed with diethylether and dried under vacuum giving the hydrochloride salt of 54 as a tan solid (0.143 g).

Provenance & Evidence