Delépine胺合成反应
烷基卤代物和六亚甲基四胺反应得到铵盐,接着用HCl乙醇溶液酸解得到伯胺的反应。反应机理和Gabriel反应(产物为胺),Sommelet反应(产物为醛)类似。对于Delépine反应, 活性卤代物(如苄基卤代物,烯丙基卤代物和α-卤代酮)的反应效果都很好。
优点为底物易得,副反应少,反应步骤简单,条件温和。六亚甲四胺已为叔胺,第一步只能在氮上引入一个烷基,因此水解后生成比较纯净的伯胺。
反应机理
经过 SN2 反应得到六亚甲基四铵盐,在氯仿中,原料是可溶的反应后产物可以结晶出来,通常不需要继续纯化。
反应实例
参考文献
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编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Delépine amine synthesis,page 198-199.