Метоксамин

Vasoxyl ,Burroughs-Wellcome,US,1949

2,5-Dimethoxypropiophenone is treated in absolute ether with methyl nitrite and hydrogen chloride. The hydrochloride of 2,5-dimethoxy-αisonitrosopropiophenone crystallizes out of the solution. It is removed, the base is liberated and crystallized from benzene-heptane forming yellow leaflets that melt at about 97° to 98°C. This isonitrosoketone is dissolved in absolute alcohol containing an excess of hydrogen chloride and is hydrogenated with palladized charcoal, yielding β-(2,5-dimethoxyphenyl)-βketoisopropylamine hydrochloride, a salt that melts at about 176°C with decomposition.
12.3 g (1/20 mol) of β-(2,5-dimethoxyphenyl)-β-ketoisopropylamine hydrochloride (MP 176°C) is dissolved in 50 cc of water and hydrogenated with platinum oxide platinum black in the customary Adams-Burgess Parr apparatus. About 1/20 mol of hydrogen is absorbed, after which the solution is filtered off from the catalyst, evaporated to dryness in vacuo and recrystallized from absolute alcohol, absolute ether being added to decrease solubility. The hydrochloride is thus obtained in substantially theoretical yield. It crystallizes in plates and melts at 215°C.

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