Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides

    • Gary Mathieu
    • Heena Patel
    • Hélène Lebel
    • Department of Chemistry and Center in Green Chemistry and Catalysis (CGCC), Université de Montréal, P.O. Box 6128, Station, Downtown, Montréal, QC H3C 3J7, Canada

    The first continuous flow process was developed to synthesize N-methyl secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-methyl secondary amines were produced in good to excellent yields, including a number of bioactive compounds, or their precursors. Up to 10.6 g (88% yield) of a N-methyl secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alcohol. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed.

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