3-氰基-4-哌啶酮盐酸盐的合成与表征  

Synthesis and Characterization of 4-Oxopiperidine-3-Carbonitrile Hydrochloride

作　　者：王赛[1] 杨明 王佩[1] 黄龙江[1] 

机构地区：[1]青岛科技大学化工学院,山东青岛266042 [2]山东省质量技术审查评价中心,山东济南250014

出　　处：《化学与生物工程》2017年第3期27-30,共4页Chemistry & Bioengineering

基　　金：山东省高校科技计划资助项目(J16LC13)

摘　　要：以β-丙氨酸甲酯盐酸盐和丙烯腈为原料,经氨基的迈克尔加成、Boc(叔丁氧羰基)保护、分子内环合以及脱保护等4步反应制备了3-氰基-4-哌啶酮盐酸盐,总收率73.7%。对关键的杂原子的迈克尔加成和分子内环合的反应条件进行了优化,得到了迈克尔加成反应较佳的工艺条件:甲醇为溶剂,甲醇钠为碱,丙烯腈∶β-丙氨酸甲酯盐酸盐∶甲醇钠为1.25∶1∶1(物质的量比),反应温度为50℃,反应时间为6h;环合反应较佳的工艺条件:以甲苯为溶剂,氢化钠为碱,反应温度为80℃,反应时间为2h。目标产物的结构经核磁共振氢谱、碳谱和质谱确证。Using β-alanine methyl ester hydrochloride and acrylonitrile as raw materials, 4-oxopiperidine-3- carbonitrile hydrochloride was synthesized by the reaction of Michael addition,Boc（t-butyloxycarboryl） protec- tion,intramolecular cyclization and de-protection with the total yield of 73.7%. The reaction conditions of key heteratomic Michael addition and intramolecular cyclization were optimized. The optimal conditions of Michael addition were as follows： the solvent of methanol, the alkali of sodium methoxide, the molar ratio of acryloni- trile ： β-alanine methyl ester hydrochloride ： sodium methoxide= 1.25 ： 1： 1, reaction temperature 50 ℃, reac- tion time 6 h;the optimal conditions of cyclization were as follows： the solvent of toluene,the alkali of sodium hydride, reaction temperature 80 ℃, reaction time 2 h. The structure of the target product was confirmed by ^1HNMR,^13CNMR and MS.

关 键 词：3-氰基-4-哌啶酮盐酸盐 迈克尔加成 环合 

分 类 号：TQ463[化学工程—制药化工]