Sodium Chloride → 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate

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Reaction Steps

1.80 g of N-[6-chloro-2-(4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 20 hours under argon in 17 ml of ethylene glycol/water 12:5 in the presence of 0.9 g of potassium hydroxide. The mixture was left to cool and was treated with 140 ml of semi-saturated sodium chloride solution. The mixture was extracted three times with diethyl ether. The combined extracts were washed once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The brown oil was chromatographed on 50 g of silica gel with dichloromethane/methanol (19:1, then 9:1). The crude product was dissolved in 7 ml of diethyl ether and 0.98 g of fumaric acid was added. The solvent was removed in a vacuum and the residue was recrystallized from 50 ml of chloroform/ethanol 4:1. 1.41 g (62%) of 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) with m.p. 187°-188° were obtained.

Provenance & Evidence