Methanol → 3-(5-Methoxy-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene hydrochloric acid salt

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Reaction Steps

3-(5-Methoxy-benzo[b]thiophen-2-yl)-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene (2.28 g, 7.99 mmol) was solved in toluene (25 ml). 1-Chloroethylchloroformate (2.28 g, 15.97 mmol) was added at room-temperature. The mixture was stirred at room-temperature for 1 hour and was then stirred at reflux for 15 hours. Methanol (20 ml) was added followed by reflux for 2 hours. The mixture was cooled on an ice-bath. The product crystallized and was washed with ethanol and diethylether. The product was recrystallised from ethanol as hydrochloric acid salt, yield 0.37 g (15%). The mother liquor was evaporated, converted to the free base by adding aqueous ammonia and extraction with dichloromethane followed by chromatographic purification using dichloromethane, methanol and aqueous ammonia (9:1+1%). Yield 0.30 g (14%).

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