Cyclopropylamine Synthesis

This paper introduced the usage . research background and main routes of synthesizing cyclopropylamine and cyclopropanecarboxylic acid. The paper analyzed the advantages and the disadvantages of every synthesizing route briefly. According to the character of cyclopropylamine and cyclopropanecarboxylic acid, the author decided to synthesize cyclopropylamine by six steps. Iso-propyl- γ chlorobutyrate. cyclopropanecarboxylic acid isopropy cyclopropanecarboxylic acid . cyclopropanecarbonyl chloride cyclopropanecarboxamide and cyclopropylamine were synthesized in order. The improvement of synthesizing iso-propyl- γ chlorobutyrate from γ -butyrolactone . sulfur oxychloride and iso-propyl alcohol at normal atmospheric temperature and atmosphere at one step was investigated, unseperating the intermediate- γ -chlorobutyryl chloride or γ -chlorobutyric acid. A series of experiments were proceeded through analyzing all kinds of factors which affect the reaction and the author got a good conclusion. The yield of iso-propyl- γ -chlorobutyrate was beyond of 93%,based on γ -butyrolactone. Cyclopropanecarboxylic acid isopropyl was synthesized from iso-propyl- γ chlorobutyrate and sodium hydroxide. This reaction was catalyzed by phase transfer catalyst(PTC). Benzene and water could form azeotropic mixture and the water produced during the reaction was discharged azeotropically. A series of experiments were proceeded through analyzing all kinds of factors which affect the reaction.The yield was beyond of 73%, based on iso-propyl- γ chlorobutyrate. Cyclopropanecarboxylic acid was synthesized from cyclopropanecarboxylic acid isopropyl by liquid-liquid phase transfer catalysis. By optimizing the factors which affect the reaction, the hydrolytic yield was 84.2%, based on cyclopropanecarboxylic acid isopropyl. Cyclopropanecarbonyl chloride was synthesized by reaction of cycolpropanecarboxylic acid and sulfur oxychloride. By optimizing the factors which affect the reaction, the yield was 97.2%, based on cycolpropanecarboxylic acid. Ethyl acetate acted as solvate and the temperature was 0℃. On this condition we let cyclopropanecarbonyl chloride react with ammonia and got cyclopropanecarboxamide. The yield was 95.6%, based on cyclopropanecarbonyl chloride. Cyclopropylamine was preparated by Hofmann degradation of cyclopropanecarboxamide. The yield was %. According to the physical character and chemical character of all intermediates and cyclopropylamine,.these synthetics were qualitatively analysized and quantitatively analysized by using traditional titration and modern analytical methods (IR, GC, GC-MS) .