Water → HCID 14349109, compound

Participants

Reaction Steps

A solution of 7,8-dimethoxy-1-(4-nitrophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 49, (6 g, 17.4 mmole) in 25 ml 95% formic acid and 25 ml 37% aqueous formaldehyde solution was stirred at 75° C. for 1.5 hours. After cooling, the reaction mixture was stirred with water, basified with sodium carbonate and was extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride and was dried (anhydrous MgSO4), filtered and evaporated to 6.2 g of an oil. This oil was purified by high pressure liquid chromatography (silica gel, ethyl acetate) to give 4.6 g (74%) of an oil. This oil was converted to the oxalate salt as in Example 1 and was twice recrystallized from isopropanol-methanol to give 3.4 g (44) of 7,8-dimethoxy-3-methyl-1-(4-nitrophenoxy)-2,2,4,5-tetrahydro-3-benzazepine oxalate, d 158°-159° C.

Provenance & Evidence