Synthesis And Process Improvement Of Homopiperzine

Homopiperzine is an important chemical material and pharmaceutical intermediate. It could be used in the synthesis of a number of fine chemicals including pharmaceuticals, pesticides, dyestuffs surfactants, etc. in this study, from ethylenediamine, as homopiperzine, were prepared via sulfonylation,cyclization and detosylation three-step reaction. Removal of the N-tosyl from the N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine by alkali method for the first time, the yield of homopiperzine was more than 95%. Synthesis of N,N′-1,4-bis(4-methylphenyl)sulfonyl-ethylenediamine,N,N′-1,4-bis(4-methyl- phenyl) sulf- only-homopiperzine and homopiperzine was investigated in this paper. The better technological conditions have been obtained via the experiments and the products have been characterized.The better technological conditions of N,N′-1,4-bis(4-methylphenyl)sulfonyl- ethylene- diamine's synthesis have been obtained, the molar ratio of ethylenediamine, p-methylbenzene sulfonic chloride and sodium hydroxide was 1:2.5:0.2 with 2.25g (0.0375mmol) ethylene- diamine, the reactive temperature was 25℃, the reactive time was5 h, solvent volume of was 6mL. The molar yield of the product could reach 88.8% under this technological conditions.The better technological conditions of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homo- piperzine's synthesis have been obtained, N,N′-1,4-bis(4-methylphenyl)sulfonyl-ethylene -diamine 0.02mol, the molar ratio of N,N′-1,4-bis(4-methylphenyl)sulfonyl-ethylene-diamine to 1,3-dibromopropane is 1:1.5, the reaction time was 13 hours, solvent volume of dimethylformamide was 70mL, phase transfer catalyst was 0.6g , the best yield of the structure could reach 70.9%.The better technological conditions of homopiperzine's synthesis have been obtained, the molar ratio of N,N′-1,4-bis(4-methylphenyl)sulfonyl-homopiperzine and sodium hydroxide was 1:2.5 with 40.9g(0.1mol) N,N′-1,4-bis(4-methylphenyl) sulfonyl-homo-piperzine, the reactive temperature was 70℃, the reactive time was3 h, solvent volume of was 60mL. The molar yield of the product could reach 95.7% under this technological conditions.Under these conditions, the yield of homopiperzine was about 60%. The reaction conditions was much moderate compared to references. At the same time, this method also has many advantages, such as pure products, few catalysts, easy post processing, easy operation, safety, little pollution and so on. There had instructional effects for the industrialization of homopiperzine .