Paper
Cyclization of N,N-Bis(2-chloroethyl)methylamine in Aqueous Hydrazine
Published Jul 1, 2004 · P. M. Kushakova, V. А. Kuznetsov, A. Chernobroviy
Chemistry of Heterocyclic Compounds
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Abstract
1-Amino-4-methylpiperazine (1) is widely used as an intermediate in synthesis of medicinal drugs [1]. Several methods for obtaining it are known. A method based on a two-step scheme has been used industrially, starting from piperazine and followed by its nitrosation and reduction [2, 3]. We have obtained compound 1 for the first time by reaction of N,N-bis(2-chloroethyl)methylamine (2) with an aqueous solution of hydrazine, and we have also developed an efficient method for its isolation. Analysis of the literature [3, 4] allowed us to determine the optimum ratio of the reagents when the dihalo derivative is used as the substrate. In the temperature range 40-50°C, the ratio of the reagents is substrate 1:N2H4 (50%) 1:10. Analysis of the reaction mass using GLC data, chromatography/mass spectrometry, and C NMR showed that along with the target product 1, a number of impurities are formed which we identified.
This study developed an efficient method for obtaining 1-amino-4-methylpiperazine from N,N-bis(2-chloroethyl)methylamine and hydrazine, with potential applications in medicinal drug synthesis.
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