2-(三甲氧基苯基)色胺盐酸盐的合成

2,3,4-及3,4,5-三甲氧基苯乙酮苯腙在多聚磷酸存在下进行Fischer反应,可生成相应的吲哚(1_a,1_b),但2,4,6-三甲氧基苯乙酮苯腙必须用无水氯化锌催化环化才能得到相应的吲哚(1_c)。1_a、1_b、1_c经Vilsmier反应生成相应的吲哚-3-醛(2_a,2_b,2_c);经与硝基甲烷缩合得到相应的2-(三甲氧基苯基)-3-(2-硝基乙烯基)吲哚(3_a,3_b,3_c);3_a及3_b用LiAlH₄还原即可制备成相应的色胺盐酸盐(4_a和4_b),3_b还被制成苦味酸盐(4_b)。

Synthesis of 2-(Trimcthoxyphenyl) Tryptamines Hydrochloride

In the presence of PPA, 2- ( 2, 3, 4- trimethoxyphenyl) indole ( 1a) and 2-(3,4,5-trimethoxyphenyl) indole (1b) were prepared by the Fischer synthesis from the corresponding trimethoxyacetophenone phenylhydrazones. 2-(2, 4 , 6-Trimethoxyphenyl)indole(1c) was prepared by treating 2, 4,6-trimethoxy acetophenone phenylhydrazone with anhydrous zinc chloride. 1a, 1b, 1c were converted to the 3-formyl derivatives 2a, 2b, 2C under Vilsmier reaction conditions , respectively, and 2,, 2b, 2C were condensed with nitromethane to give the corresponding 3-(2-nitroethenyl)in-doles 3a, 3b and 3C. Reduction of 3a or 3b with LiAlH, gaves the corresponding tryptamines 4, and 4b, respectively.