Hydrochloric Acid → HCID 131718437, compound

Participants

Reaction Steps

6.28 g (0.016 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-morpholinoethyl)-1H-benzo[e]indole hydrochloride were dissolved in 0.51 of 48 percent aqueous HBr, boiled under reflux for 4 hours and then concentrated, whereupon the residue was dissolved in water. The solution was neutrallized by adding firstly solid Na2SO3 and then saturated aqueous NaHCO3 solution. The mixture was extracted three times with CH2Cl2, the organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered, the filtrate was concentrated and the residue was chromatographed over 0.27 kg of silica gel with methylene chloride/methanol (4:1). The product (4.8 g) was dissolved in 150 ml of ethanol. 6 ml (0.035 mol) of 21 percent ethanolic HCl solution were added dropwise thereto and the mixture was stirred at room temperature for 4 hours, whereby crystals separated. Recrystallization from ethanol gave 4.97 g (82%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(2-morpholinoethyl)-1H-benzo[e]indol-6-ol dihydrochloride as white crystals with m.p. 230°-275° (dec.).

Provenance & Evidence