Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Solvent Free N-Heterocyclization of Primary Amines to N-Substituted Azacyclopentanes Using Hydrotalcite as Solid Base Catalyst

  • Dixit, Manish (Department of Chemical Engineering And Shah-Schulman Center for Surface Science and Nanotechnology, Faculty of Technology, Dharmsinh Desai University) ;
  • Mishra, Manish (Department of Chemical Engineering And Shah-Schulman Center for Surface Science and Nanotechnology, Faculty of Technology, Dharmsinh Desai University) ;
  • Joshi, P.A. (Department of Chemical Engineering And Shah-Schulman Center for Surface Science and Nanotechnology, Faculty of Technology, Dharmsinh Desai University) ;
  • Shah, D.O. (Department of Chemical Engineering And Shah-Schulman Center for Surface Science and Nanotechnology, Faculty of Technology, Dharmsinh Desai University)
  • Received : 2011.11.12
  • Accepted : 2012.01.30
  • Published : 2012.05.20
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Abstract

An ecofriendly catalytic route for selective synthesis of $N$-substituted azacyclopentanes, nitrogen-containing heterocyclic intermediates for many bioactive compounds, was established by carrying out $N$-heterocyclization (di $N$-alkylation) of primary amines with 1,4-dichloro butane (as dialkylating agent) using catalytic amount of hydrotalcite as solid base catalyst. The hydrotalcite was found to be efficient solid base catalyst for di $N$-alkylation of different primary amines (aniline, benzyl amine, cyclohexyl amine and n-butyl amine) giving 82 to 96% conversion (at optimized reaction condition) of 1,4-dichloro butane and > 99% selectivity of respective $N$-substituted azacyclopentanes within 30 min. under solvent free condition. The reaction parameters significantly influence the conversion of 1,4-dichloro butane to $N$-substituted azacyclopentanes. The nature of substituent present on amino group affects the reactivity of amine substrates for di $N$-alkylation reaction with 1,4-dichloro butane. The 1,4-dichloro butane was found to be highly reactive alkylating agent for di $N$-alkylation of amines as compared to 1,4-dihydroxy butane. The reusability of the catalyst and its chemical stability in the reaction was demonstrated.

Keywords

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