N-(3-吡啶基甲基)氮杂环化合物的合成  

Synthesis of N-(3-Pyridylmethyl) Heterocyclic Compounds

作　　者：段学民[1] 韩娟[1] 陈立功[1] 许艳杰[1] 李阳[1] 

机构地区：[1]天津大学药物科学与技术学院,天津300072

出　　处：《精细化工》2005年第1期39-40,52,共3页Fine Chemicals

摘　　要：以3 氯甲基吡啶盐酸盐和含氮杂环化合物四氢吡咯、哌啶、吗啉、哌嗪及咔唑为原料,通过N 烷基化反应,合成了6个N (3 吡啶基甲基)氮杂环化合物。3 氯甲基吡啶盐酸盐分别与四氢吡咯、哌啶、吗啉在二甲亚砜中于50℃下反应3h,后在室温下反应16h,得到N (3 吡啶基甲基)四氢吡咯、N (3 吡啶基甲基)哌啶及N (3 吡啶基甲基)吗啉,收率分别为87 1%、85 5%和73 1%;3 氯甲基吡啶盐酸盐与无水哌嗪以不同的投料比〔n(3 氯甲基吡啶盐酸盐)∶n(无水哌嗪)=1∶2 67和3∶1),分别在甲醇中于50℃下反应8h和10h,得到N (3 吡啶基甲基)哌嗪和N,N′ 二(3 吡啶基甲基)哌嗪,收率分别为82 4%和61 3%;3 氯甲基吡啶盐酸盐与咔唑在N,N 二甲基甲酰胺中于室温下反应12h,得到9 (3 吡啶基甲基)咔唑,收率93 7%。用1HNMR和13CNMR对产品进行了表征,证明了合成方法的可靠性。Six N-(3-pyridylmethyl) N-containing heterocyclic compounds were obtained by N-alkylation of 3-chloromethylpyridine hydrochloride with N-containing heterocyclic compounds including pyrrolidine,piperidine,morpholine,piperazine and carbazole.Pyrrolidine,piperidine and morpholine were respectively treated with 3-chloromethylpyridine hydrochloride in DMSO at 50 ℃ for 3 h and then at room temperature for 16 h to afford N-(3-pyridylmethyl)pyrrolidine,N-(3-pyridylmethyl)piperidine and N-(3-pyridylmethyl)morpholine in 87.1%,85.5% and 73.1% yield.3-Chloromethylpyridine hydrochloride reacted with piperazine in different ratios 〔n(3-chloromethylpyridine hydrochloride)∶n(piperazine)=1∶2.67 and 3∶1〕 in methanol at 50 ℃ for 8 h and 10 h respectively to give N-(3-pyridylmethyl)piperazine and N,N′-bis(3-pyridylmethyl)piperazine in 82.4% and 61.3% yield.Carbazole was treated with 3-chloromethylpyridine hydrochloride in DMF at room temperature for 12 h to afford 9-(3-pyridylmethyl)carbazole in 93.7% yield.The products were characterized by^1HNMR and^(13)CNMR.The results showed the reliability of the synthetic method.

关 键 词：3-氯甲基吡啶盐酸盐 含氮杂环化合物 N-烷基化 

分 类 号：TQ460.31[化学工程—制药化工]