Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine

Joshua Britton, Justin Chalker, Colin Raston

    Research output: Contribution to journalArticlepeer-review

    37 Citations (Scopus)

    Abstract

    Thin film flow chemistry using a vortex fluidic device (VFD) is effective in the scalable acylation of amines under shear, with the yields of the amides dramatically enhanced relative to traditional batch techniques. The optimized monophasic flow conditions are effective in ≤80seconds at room temperature, enabling access to structurally diverse amides, functionalized amino acids and substituted ureas on multigram scales. Amide synthesis under flow was also extended to a total synthesis of local anesthetic lidocaine, with sequential reactions carried out in two serially linked VFD units. The synthesis could also be executed in a single VFD, in which the tandem reactions involve reagent delivery at different positions along the rapidly rotating tube with in situ solvent replacement, as a molecular assembly line process. This further highlights the versatility of the VFD in organic synthesis, as does the finding of a remarkably efficient debenzylation of p-methoxybenzyl amines.

    Original languageEnglish
    Pages (from-to)10660-10665
    Number of pages6
    JournalChemistry-A European Journal
    Volume21
    Issue number30
    DOIs
    Publication statusPublished - 1 Jul 2015

    Keywords

    • acylations
    • amides
    • amino acids
    • flow chemistry
    • synthetic methods

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