Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1695-1702.DOI: 10.6023/cjoc201801029 Previous Articles     Next Articles



朱兰平, 赵帅, 仓志鹏, 周安迪, 陈新   

  1. 常州大学制药与生命科学学院 常州 213164
  • 收稿日期:2018-01-21 修回日期:2018-03-07 发布日期:2018-04-04
  • 通讯作者: 陈新
  • 基金资助:


An Efficient Method for the Synthesis of 2-Methyl-1-substituted-phenyl-2-propylamines

Zhu Lanping, Zhao Shuai, Cang Zhipeng, Zhou Andi, Chen Xin   

  1. School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164
  • Received:2018-01-21 Revised:2018-03-07 Published:2018-04-04
  • Contact: 10.6023/cjoc201801029
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272029).

2-Methyl-1-substituted-phenyl-2-propylamines are key intermediates for synthesizing the β2 adrenoceptor agonists. A series of 2-methyl-1-substituted-phenyl-2-propylamines have been synthesized starting from substituted benzyl chlorides. Isobutyronitrile was alkylated with benzyl chloride, and the resulting 2-methyl-1-aryl-2-butylcynide was hydrolyzed to give the corresponding acid. Curtius rearrangement of the acid and catalytic hydrolgenation of the resulting Cbz-protected amine afforded the title compound. The method is simple and safe to operate, the raw materials are readily available and the overall yields are satisfactory. This method is suitable for the synthesis of 2-methyl-2-(2-methylphenyl)-phenyl-2-propylamine and various kinds of derivatives.

Key words: 2-methyl-1-substituted-phenyl-2-propylamine, β2 adrenoceptor agonist, Curtius rearrangement, synthesis