S(=O)(=O)(O)O.[CH2:6]1[CH:10]2[C:11]3[C:16]([CH2:17][CH2:18][N:9]2[CH2:8][CH2:7]1)=[CH:15][CH:14]=[CH:13][CH:12]=3.[N+:19]([O-])([O-:21])=[O:20].[K+].[OH-].[NH4+].[ClH:26].C(O)(C)C>C(O)(C)C>[ClH:26].[N+:19]([C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][CH2:18][N:9]3[CH2:8][CH2:7][CH2:6][CH:10]32)=[CH:15][CH:14]=1)([O-:21])=[O:20]To concentrated sulfuric acid (200 ml) at -10° C. was added portionwise 1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline (20.5 g, 118 mmol) over 2 h. After addition was complete, potassium nitrate (1 1.6 g, 0.115 mol) was added portionwise over 3 h. The reaction mixture was stirred for an additional 3 h and then poured onto ice and made basic with concentrated ammonium hydroxide. The product was extracted twice with dichloromethane. The dried (magnesium sulfate) organic phase was concentrated to give a red oil which was immediately dissolved in isopropanol (200 ml) and made acidic with saturated isopropanol-HCl. The resulting precipitate was collected to give a tan solid (18.9 g). Recrystallization from 95% ethanol (100 ml) afforded the title compound as an off-white solid (11.5 g, 62%), m.p. 243-5° C. This was converted to the free base by dissolving in water, making basic with dilute base, and extracting with dichloromethane to give 96% recovery of the product.
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