Pyrrolidine amine oxide Transformation

Double bonds between carbon and nitrogen in secondary and tertiary cyclic amines are formed on treatment with mercuric acetate [401, 402, 1091], silver oxide [375], or tert-butyl hypochlorite [707]. tert-Butyl hypochlorite converts methyl pyrrolidine-2-carboxylate into methyl 1-pyrrol ine-2-carboxylate in 71% yield [707], and mercuric acetate transforms 2-terr-butylpiperidine into 2-tm-butyl-l-piperideine in 75% yield [1091]. Tertiary cyclic amines are dehydrogenated by mercuric acetate via quaternary salts [401,402]. l-Methyl-2-ethylpiperidine yields ultimately 1-methyl-2-ethyl-2-piperideine [402] and quinolizidine A -dehydroquin-olizidine [401] (equation 34). 

Pyrrolidine and TV-substituted pyrrolidines are produced commercially by ring transformation of tetrahydrofuran with ammonia or primary amines at 300°C on aluminium oxide catalysts. 

Pyrrolidine and N-substituted pyrrolidines are produced technically by ring transformation of THF with ammonia or primary amines at 300 °C on aluminum oxide catalysts. N-Substituted pyrrolidines are also accessible by photodehydrohalogenation of N-alkyl-N-chloroamines (Hofmann-Loffler reaction) ... 

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