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Convenient N-Alkylation of amines using an effective magnetically separable supported ionic liquid containing an anionic polyoxometalate

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Abstract

An effective synthesis of anion-exchanged supported ionic liquid using magnetically separable nanoparticles and its catalytic effect on N-alkylation reactions is described. Anionic polyoxometalate derivative was used in the anion-exchange step in catalyst design. The catalytic system can be easily separated from the reaction mixture with external magnetic field and recycled in subsequent reactions. In order to evaluate catalyst repeatability, N-alkylation of some more amines such as Aniline, 4-aminobenzenesulfonamide, 4-methoxyaniline, 2-aminopyrimidin and 4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine in the presence of recoverable catalyst was successfully examined in this article. In addition, pramipexole dihydrochloride as an active pharmaceutical ingredient was successfully synthesized using the catalytic system. The structure of catalyst was determined by infrared spectroscopy, X-ray powder diffraction, and scanning electron microscope techniques. The structure of organic products was determined by 1H NMR, 13C NMR, infrared and Mass spectroscopy.

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Acknowledgments

The authors wish to gratefully thank the Research Affairs Division at Amir Kabir University of Technology (AUT), Tehran, for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Amirkabir University of Technology, Hafez Avenue, No. 424, Tehran, Islamic Republic of Iran

    Mohammad Hadi Ghasemi & Elaheh Kowsari

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  1. Mohammad Hadi Ghasemi
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  2. Elaheh Kowsari
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Correspondence to Elaheh Kowsari.

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Ghasemi, M.H., Kowsari, E. Convenient N-Alkylation of amines using an effective magnetically separable supported ionic liquid containing an anionic polyoxometalate. Res Chem Intermed 43, 1957–1968 (2017). https://doi.org/10.1007/s11164-016-2741-2

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  • DOI: https://doi.org/10.1007/s11164-016-2741-2

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