Abstract
Cyclopropylamine is synthesized with γ-butyrolactone and isopropanol by five steps of ring-opening esterification, cyclization, hydrolysis, acylation and Hofmann degradation. Cyclization and hydrolysis are key steps in the process, and Phase Transfer Catalysis (PTC) is used in the two steps respectively. In the cyclization reaction, because solid-liquid PTC, sodium hydroxide is applied instead of expensive sodium alcoholate, the reaction can be carried out in mild conditions. The optimum reaction conditions are as follows: 0.03:1:1.5 mole ratio of BTEAC to ester to sodium hydroxide, reacting at 50 °C for 2 h with yield of 92%. Hydrolysis of isopropyl cyclopropanecarboxylate is accelerated by liquid-liquid PTC, and the order of catalytic activity is BTEC > BTMAC > CTMAB > TBAB. The results show that the new synthesis method is superior to those from literature and feasible for production with simple routes, mild reaction conditions, cheap materials and total yield of 52.6%.
Similar content being viewed by others
References
Joseph T Blackwell, Denham S. Process for the manufacture of cyclopropylamine[P]. US Pat, No. 4590292. 1986
Cahoy Roger P, Phillips L V. Cyclopropylamine from butyrolactone[P]. Ger Offen Pat, No. 1939759. 1970
LI He-ping, GE Hong, ZHANG Fu-qiang. New technology for synthesis of cyclopropylamine[J]. Chemical World (in Chinese), 1997, 38(7): 358–360
ZHAO Xue-qing, ZHANG Yuan. Synthesis of cyclopropylamine[J]. Chinese Journal of Pharmaceuticals (in Chinese), 1994, 25(5): 225
LI Mei, GUO Hui-yuan. Graphical synthetic routes of cyclopropylamine[J]. Chinese Journal of Pharmaceuticals (in Chinese), 1992, 23(3): 141
Author information
Authors and Affiliations
Additional information
Foundation item: The Science and Research Foundation of Education Commission of Hunan Province
Biography of the first author: YI Jian-ming, associate professor, born in 1957, majoring in applied chemistry.
Rights and permissions
About this article
Cite this article
Yi, Jm., Tang, Kw., Ren, By. et al. Synthesis of cyclopropylamine with phase transfer catalysis. J Cent. South Univ. Technol. 7, 81–83 (2000). https://doi.org/10.1007/s11771-000-0037-5
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11771-000-0037-5