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4,4′-Trimethylenedipiperidine, a safe and greener alternative for piperidine, catalyzed the synthesis of N-methyl imines

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Abstract

A practical and facile synthesis of various N-methyl imines, versatile scaffolds, was conducted at 85 °C using 4,4′-trimethylenedipiperidine as a safe and green catalyst. This reagent is a commercially available solid and can be handled easily. It has high thermal stability, low toxicity, and good solubility in green solvents such as water and ethanol. The regenerated catalyst demonstrated stable activity after several recycle runs, and any changes were detected in its chemical structure by 1H NMR monitoring. The novelty of the current work is that the 4,4′-trimethylenedipiperidine can act as a promising alternative for piperidine in organic reaction at higher temperatures due to its broad liquid range temperature, thermal stability, acceptor/donor hydrogen bond property, and other unique merits. Furthermore, the current protocol avoids waste generation in the workup process, which is a drawback in most previous reported procedures.

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Acknowledgements

The authors used a Research Grant (IF065-2020) from Japan International Cooperation Agency (JICA), Japan, to conduct this work. The authors are also grateful to all staff members in the Analytical and Testing Center of Nanotechnology and Catalysis Research Center of Universiti Malaya for their partial support.

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Authors and Affiliations

  1. Department of Food Science and Technology, Sari Agricultural Sciences and Natural Resources University, Sari, Iran

    Hayedeh Gorjian & Nader Ghaffari Khaligh

  2. Nanotechnology and Catalysis Research Center, Institute for Advanced Studies, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Nader Ghaffari Khaligh

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  1. Hayedeh Gorjian
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  2. Nader Ghaffari Khaligh
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Correspondence to Nader Ghaffari Khaligh.

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Gorjian, H., Khaligh, N.G. 4,4′-Trimethylenedipiperidine, a safe and greener alternative for piperidine, catalyzed the synthesis of N-methyl imines. Res Chem Intermed 48, 2035–2045 (2022). https://doi.org/10.1007/s11164-022-04680-2

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