应用化学

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N-(3-氨基丙基)甲基丙烯酰胺盐酸盐的新合成路线

戴鹏1,肖云杰1,王泽瑜1,陈世坤1,何同胜2,申永存1*   

  1. (1.武汉理工大学化学工程学院 武汉 430070;2.武汉志邦化学技术有限公司 武汉 430070)
  • 收稿日期:2013-01-28 修回日期:2013-04-01 出版日期:2013-11-10 发布日期:2013-11-10
  • 通讯作者: 申永存,教授; Tel/Fax:027-87859019; E-mail:sycmichael@163.com; 研究方向:不对称合成和手性药物
  • 基金资助:
    大学生创新基金

A New Synthetic Route of N-(3-Aminopropyl)methacrylamide Hydrochloride

DAI Peng1, XIAO Yunjie1, WANG Zeyu1, CHEN Shikun1, HE Tongsheng2, SHEN Yongcun1*   

  1. (1.Chemical Engineering College,Wuhan University of Technology,Wuhan 430070,China;
    2.Wuhan Zhibang Chemical Technology Co. Ltd.,Wuhan 430070,China)
  • Received:2013-01-28 Revised:2013-04-01 Published:2013-11-10 Online:2013-11-10
  • Contact: Micheal

摘要: 以3-氯丙胺盐酸盐(Ⅰ)为原料,经甲基丙烯酸酐酰化得到N-(3-氯丙基)甲基丙烯酰胺(Ⅱ)后, 通过Gabriel合成法得到N-[N′-(甲基丙烯酰基)-3-氨基丙基]邻苯二甲酰亚胺(Ⅲ)和肼解产物N-(3-氨基丙基)甲基丙烯酰胺(Ⅳ),再经盐酸化得到N-(3-氨基丙基)甲基丙烯酰胺盐酸盐(Ⅴ),全程收率可达61.1%。 该工艺中无需使用价格昂贵的氨基保护试剂,可极大降低原料成本。

关键词: 氯丙胺盐酸盐, N-(氨基丙基)甲基丙烯酰胺盐酸盐, 工艺改进

Abstract: A new method to prepare N-(3-aminopropyl) methacrylamide hydrochloride(Ⅴ) was introduced. N-(3-Chloropropyl) methacrylamide(Ⅱ), obtained by acylation reaction between 3-chloropropylamine-hydrochloride(Ⅰ) and methacrylic anhydride, was transformed via Gabriel method to N-[N′-(methacryl)-3-aminopropyl] phthalimide(Ⅲ) and hydrazinolysis product N-(3-aminopropyl) methacrylamide(Ⅳ) and then hydrochloric acidification to compound Ⅴ. The overall yield of the reaction is about 61.1%. This process does not need to use any expensive amino protection reagent, which can dramatically reduces the cost of raw materials.

Key words: chloropropylamine hydrochloride, N-(aminopropyl)methacrylamide hydrochloride, process improvement

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