An improved procedure for the synthesis of 2-morpholinoethanamine

Research on Chemical Intermediates - Tập 36 - Trang 523-528 - 2010
Ri-sheng Yao1,2, Sheng-hua Wu1, Lai-en Jiang1, Sheng-song Deng1, San-xi Yu3
1Department of Pharmaceutical Engineering, Hefei University of Technology, Hefei, China
2Engineering Research Center of Bioprocess, Ministry of Education, Hefei University of Technology, Hefei, China
3Ansheng Biochemical Sci & Tech Co. Ltd., Hefei, China

Tóm tắt

2-Morpholinoethanamine is prepared rapidly mainly in aqueous conditions from inexpensive and commercially accessible starting materials. The process development of an effective synthetic route by utilizing morpholine as the starting material via Michael addition, hydrazinolysis, and Curtius rearrangements was undertaken. The optimal conditions were selected in the experiments. The total yield was 81.8% and it was a convenient process.

Tài liệu tham khảo

W.B. Reinach, P.C. Muttenz, U.S. Patent 1980/4, 210, 754 (1980) C.L.E. Broekkamp, D. Leysen, B.W.M.M. Peeters, R.M. Pinder, J. Med. Chem. 38(23), 4615–4633 (1995) A.H. Elias, D.T. Manallack, I.B. Bestel, H.R. Irving, I.M. Coupar, M.N. Iskander, J. Med. Chem. 44, 2952–2959 (2009) E.F. DiMauro, J. Newcomb, J.J. Nunes, J.E. Bemis, C. Boucher, J. Med. Chem. 49, 5671–5686 (2006) I.G. Monterrey, P. Campiglia, A. Carotenuto, P. Stiuso, A. Bertamino, J. Med. Chem. 51, 2924–2932 (2008) R.S. Yao, L.E. Jiang, S.S. Deng, Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 101613246 (2009) (in Chinese) J.P. Mason, S. Malkiel, J. Am. Chem. Soc. 62(6), 1448–1450 (1940) K. Nakaging, Nippon Kagakn Zasshi 81, 1129 (1960) J.P. Mason, H.W. Block, J. Am. Chem. Soc. 62(6), 1443–1448 (1940) S. Kawahara, H. Kawakami, Yakmgakn Zasshi 81, 149 (1961) D.C. Gong, Q. Zhou, M. Qiu, Hubei Chem. (Hubei Huagong) 3, 25–26 (2000) (in Chinese) J.R. Cummings, J.B. Coun, Marshall Rev. 2, 8 (1939) S.Q. Zhou, Jiangsu Chem. (Jiangsu Huagong) 24(3), 31–32 (1996) (in Chinese) D.C. Gong, R.M. Zhao, J. Zhang, Chin. Pharm. Ind. (Zhongguo Yiyao Gongye Zazhi) 32(9), 423–424 (2001) (in Chinese) Z.Y. Cheng, L.L. Cai, Chin. Pharm. Ind. (Zhongguo Yiyao Gongye Zazhi) 25(3), 100–101 (1994) (in Chinese) L.L. Cai, S.Z. Zhang, Z.Y. Cheng, Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1094040A (1994) (in Chinese) Z. Duan, X. Xuan, T. Li, C. Yang, Y. Wu, Tetrahedron Lett. 47(31), 5433–5436 (2006)