Ammonia → HCID 20455130, compound

Participants

Reaction Steps

4.39 g. (10 mmoles) of 1-ethyl-1-(2'-methoxycarbonylethyl)-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-5-ium perchlorate are shaken with a mixture of 5 ml of 10% aqueous ammonia and 50 ml. of dichloromethane. The phases are separated, the organic phase is dried over 10 g. of solid anhydrous sodium sulfate, and then filtered. 0.5 g. of dry gaseous hydrochloric acid are introduced into the filtrate, thereafter 50 ml of glacial acetic acid are added, and dichloromethane, is distilled off in vacuo. 0.67 ml. (2.08 g., 13 mmoles) of elemental bromine are added dropwise, under vigorous stirring, to the residue at 25° C. The reaction mixture is stirred at room temperature for 3 hours, the separated product is filtered off, and suctioned well to remove the residue of acetic acid. The still wet product is suspended in 40 ml. of dichloromethane, the dilute suspension is rendered alkaline with 14 ml. of 10% aqueous ammonia, and the phases are separated from each other. The organic phase is dried over 10 g. of solid anhydrous sodium sulfate, filtered off, and the filtrate is evaporated. The obtained oily residue is triturated with 10 ml. of methanol, whereupon the product separates in crystalline form containing lattice-bound methanol. In this way 3.15 g. (70%) of 1-ethyl-1-(2'-methoxycarbonylethyl)-9-bromo-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]-quinolizin-5-ium methoxide are obtained; m.p.: 140°-142° C. The NMR spectrum of the product is identical with that given in Example 7.

Provenance & Evidence