摘要
以3-氨甲基吡啶和二苯甲酮为主要原料,以甲苯为反应介质和分水剂,以对甲苯磺酸为催化剂,先合成了3-(二苯甲酮缩亚胺基甲基)-吡啶(化合物Ⅰ),再以化合物Ⅰ为原料合成了新烟碱(化合物Ⅱ),最后以化合物Ⅱ为原料合成了新型化合物N-羧甲基新烟碱;并对化合物Ⅰ的合成条件进行了优化,同时探讨了N-羧甲基新烟碱合成过程中溴乙酸乙酯用量对中间产物结构的影响。采用1H NMR和MS等方法对所合成的化合物进行了结构表征。实验结果表明,以甲苯为溶剂,在110.6℃下回流反应4.0 h时,化合物Ⅰ的收率最高可达78.5%;当n(化合物Ⅰ)∶n(二异丙基氨基锂)∶n(顺式-1,4-二氯-2-丁烯)=1∶1.2∶1.5、反应时间3.0 h时,化合物Ⅱ的收率最高为81.5%;N-羧甲基新烟碱的收率为68.5%。
A novel compound N-carboxymethyl-anabasine was synthesized through two intermediates, N-（diphenylmethylene）（pyridin-3-yl） methanamine（compound Ⅰ ） and anatabine, in which compound Ⅰ was prepared from 3-aminomethyl pyridine and benzophenone with toluene as the reaction medium and toluene-p-sulfonic acid as the catalyst, and then anatabine was synthesis from compound Ⅰ. The synthesis conditions for compound Ⅰ were optimized, and the compounds were characterized by means of ^1H NMR and MS. The experimental results showed that the yield of compound I was 78.5% under the optimum conditions of toluene as the solvent, refluxing time 4.0 h and 110.6 ℃. When n（compound Ⅰ ） ： n（lithium diisopropylamide） ： n（cis-1, 4-dichloro-2-butene） was 1 ： 1.2 ： 1.5 and reaction time was 3.0 h, the yield of anatabine was the highest 81.5% and the yield of N-carboxymethyl-anabasine reached 68.5%.
出处
《石油化工》
CAS
CSCD
北大核心
2013年第1期69-72,共4页
Petrochemical Technology
基金
国家自然科学基金资助项目(20662007)
