N,N-二甲基色胺衍生物合成研究

Synthesis of N,N-Dimethyltryptamine Derivative

以四氢呋喃和对氰甲基盐酸苯肼 (Ⅹ )为主要原料合成了色胺衍生物N ,N 二甲基 2 { 5 [(3 氨基 1,2 ,4 口恶二唑 5 基 )甲基 ] 1 氢 吲哚 3 基 }乙胺 (Ⅶ )。四氢呋喃和氯化氢反应 ,得到4 氯丁醇 ( ) ,产率为 6 2 % ;用氯铬酸吡啶盐氧化得 4 氯丁醛 ( ) ,产率为 6 1% ;经缩醛化得 4 氯丁醛缩甲醇 ( ) ,产率为 5 6 % ;用二甲胺取代得 4 (N ,N 二甲胺基 )丁醛缩甲醇(Ⅸ ) ,产率为 86 % ;Ⅸ与Ⅹ经环化得N ,N 二甲基 2 [5 (氰甲基 ) 1氢 吲哚 3 基 ]乙胺 (Ⅺ ) ,产率为 76 % ;Ⅺ经酯化得N ,N 二甲基 2 [5 (乙酯甲基 ) 1氢 吲哚 3 基 ]乙胺 (Ⅻ ) ,产率为 82 % ;Ⅻ与羟基硫酸胍缩合得产物 (Ⅶ ) ,产率为 6 6 %。

N,N-Dimethyl-2-{5-[(3-amino-1,2,4-oxdiazol-5-yl)methyl]-1H-indol-3-yl}ethylamine(Ⅶ) was prepared with furanidine and p-cyanomethyl-phenylhydrazine(Ⅹ) as main reactants.Furanidine reacted with hydrogen chloride gas to give 4-chlorobutanol() in 62% yield. was oxidized by chloro-chromic acid pyridine salt,leading to 4-chlorobutanal() in 61% yield. was converted to 4-chlorobutanal dimethyl acetal() in 56% yield. reacted with dimethylamine to form 4-(N,N- dimethylamino)butanal dimethyl acetal Ⅸ in 86% yield.Cyclization reaction of Ⅸ with Ⅹ gave N,N- dimethyl-2-[5-(cyanomethyl)-1H-indol-3-yl]ethylamine (Ⅺ) in 76% yield.Esterification of Ⅺ gave N,N- dimethyl-2-[5-(ethoxycarbonylmethyl)-1H-indol-3-yl]ethylamine (Ⅻ) in 82% yield,Ⅻ condensed with hydroxyguanidine sulfate to form the final product Ⅶ in 66% yield.