N,N′-1,4-二对甲苯磺酰高哌嗪合成研究

Study on the synthesis of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine

以N-甲基吡咯烷酮为溶剂,NaOH为缚酸剂,1,3-二氯丙烷为环合试剂,合成N,N′-1,4-二对甲苯磺酰基高哌嗪,探究反应时间、反应物物料比、反应温度和NaOH用量对N,N′-1,4-二对甲苯磺酰基高哌嗪产率的影响。结果表明,各因素影响顺序为:碱量>温度>反应物物料比,在5 mmol N,N′-二对甲苯磺酰乙二胺,7.969 mmol 1,3-二氯丙烷,0.548 g NaOH的条件下,123℃反应40 min,N,N′-1,4-二对甲苯磺酰基高哌嗪收率可达81.93%。利用二级反应机理,在115,125,135℃三个温度下,对N,N′-1,4-二对甲苯磺酰高哌嗪合成反应进行动力学分析,得到反应的活化能为76.233 kJ/mol。

The synthesis of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine was studied with N-methylpyrrolidone as solvent,NaOH as acid binding agent and 1,3-dichloropropane as cyclization reagent.The effects of reaction time,the molar ratio of reactants,reaction temperature,and the amount of sodium hydroxide on the yield of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine were investigated.The result showed that the order of effects was as follows:alkali amount>temperature>molar ratio of reactants.The yield could reach 81.93%under the conditions of 5 mmol N,N′-bis(toluenesulfonyl)-1,2-ethylenediamine,7.969 mmol 1,3-dichloropropane and 0.548 g sodium hydroxide,123℃react 40 min.The kinetic analysis of the synthesis of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine was carried out at 115,125,135℃according to the second-order reaction mechanism,and the activation energy of this reaction was 76.233 kJ/mol.