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Molecules 2008, 13(1), 149-156; doi:10.3390/molecules13010149

Preparation of Second Generation Ionic Liquids by Efficient Solvent-Free Alkylation of N-Heterocycles with Chloroalkanes

1,* , 1
1 Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via Giuria 9, 10125 Torino, Italy 2 Laboratoire de Chimie Moléculaire et Environnement, Polytech’Savoie, Université de Savoie, 73376 Le Bourget du Lac Cedex, France 3 DSM Nutritional Products, Research and Development, NRD/CC, Building-214/071, P.O. Box 3255, CH 4002-Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 24 December 2007 / Revised: 23 January 2008 / Accepted: 23 January 2008 / Published: 25 January 2008
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Non-conventional techniques, such as microwave (MW) and power ultrasound(US) as well as combined MW/US irradiation, have been used to promote one-potsynthesis of second-generation ionic liquids (ILs), cutting down reaction times andimproving yields. However, the use of chloroalkanes in the alkylation of N-heterocyclesrequires more drastic conditions if results are to match those obtained with more reactivealkyl halides. The present paper describes a series of MW- or MW/US-promoted ILpreparations starting from chloroalkanes and classic heterocycles (1-methylimidazole,pyridine and 1-methylpyrrolidine). When reactions were carried out under conventionalheating in an oil bath they required longer reaction times and gave poorer yields. 1H-NMRanalysis and ion-exchange chromatography showed that the present solventless procedureafforded ILs of satisfactory purity. The observed high yields (usually 70-98% isolated),and short reaction times showed that a straightforward access to ILs can be also achievedwith the use of alkyl chlorides, resulting in a considerable reduction of costs.
Keywords: Ionic liquids; chloroalkanes; one-pot reaction; microwaves; ultrasound. Ionic liquids; chloroalkanes; one-pot reaction; microwaves; ultrasound.
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Cravotto, G.; Gaudino, E.C.; Boffa, L.; Lévêque, J.-M.; Estager, J.; Bonrath, W. Preparation of Second Generation Ionic Liquids by Efficient Solvent-Free Alkylation of N-Heterocycles with Chloroalkanes. Molecules 2008, 13, 149-156.

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