微波辅助合成1-(3-羟丙基)-4-哌啶酮  

Microwave assisted synthesis of 1-(3-hydroxypropyl)-4-piperidone

作　　者：王娟[1,2] 贾鹏飞 刘占荣[1,2] 刘斯婕 WANG Juan;JIA Pengfei;LIU Zhanrong;LIU Sijie(College of Chemical and Engineering,Shijiazhuang University,Shjiazhuang 050035,Hebei,China;Technology Innovation Center of Hebei for Fiber Material,Shijiazhuang 050035,Hebei,China)

机构地区：[1]石家庄学院化工学院,河北石家庄050035 [2]河北省纤维材料技术创新中心,河北石家庄050035

出　　处：《精细化工》2021年第4期801-805,共5页Fine Chemicals

基　　金：河北省重点研发计划项目(19211203D);河北省自然科学基金青年基金(H2018106015)。

摘　　要：以3-羟基丙胺和丙烯酸甲酯为起始原料,在微波辅助下进行Michael加成、Dieckmann环合和脱羧反应合成了1-(3-羟丙基)-4-哌啶酮。并对Michael加成、Dieckmann环合和脱羧反应的工艺参数进行了优化,通过核磁共振波谱对目标化合物和中间体的结构进行表征。得到的最优Michael加成工艺条件为:n(3-羟基丙胺)∶n(丙烯酸甲酯)=1.0∶2.4,微波辐射功率为120W,反应温度40℃,反应时间30min。在该条件下制备3-[(2-甲氧羰乙基)(3-羟丙基)氨基]丙酸甲酯的收率为92.6%;在微波辐射功率为200 W下,Dieckmann环合反应和脱羧反应分别为20和25 min,以88.5%的收率得到1-(3-羟丙基)-4-哌啶酮;目标产物总收率为82.0%。1-(3-Hydroxypropyl)-4-piperidone was prepared from 3-hydroxypropylamineand methyl acrylate through Michael additionreaction, Dieckmann cyclization reactionand decarboxylation reaction under microwave irradiation. The technological parameters involved in Michael additionreaction, Dieckmann cyclization reaction and decarboxylation reaction were optimized. The structures of target product and intermediate were confirmed by 1HNMR and 13CNMR. The optimal conditions for Michael addition reaction was obtained as follows: n(3-hydroxypropylamine)∶n(methyl acrylate) = 1.0∶2.4, microwave power of 120 W, reaction temperature of 40 ℃, and reaction time of 30 min. The results showed that under the above-mentioned conditions, the yield of methyl 3-[(2-methoxycarbonylethyl)(3-hydroxypropyl)amino] propionate was up to 92.6%. 1-(3-Hydroxypropyl)-4-piperidone in a yield of 88.5% was obtained when Dieckmann cyclization reaction and decarboxylation reaction was refluxed under microwave irradiation(200 W) for 20 and 25 min, respectively. The total yield of target product was 82.0%.

关 键 词：1-(3-羟丙基)-4-哌啶酮 MICHAEL加成反应 微波辐射 合成 医药原料 

分 类 号：R914.5[医药卫生—药物化学]