New convergent one pot synthesis of amino benzyl ethers bearing a nitrogen-containing bicycle |
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Authors: | Jhon J. López |
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Affiliation: | Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Concepción, Chile |
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Abstract: | We report herein a new convergent one pot method for the synthesis of amino benzyl ethers containing a bicyclic amine, derived from different substituted benzyl alcohols and bicyclic amino alcohols such as tropine, pseudotropine, and 3-quinuclidinol, using chlorotrimethylsilane and sodium iodide. In order to avoid the competitive reaction with the nitrogen atom, a solution of the separately prepared alkoxide of tropine, pseudotropine, and 3-quinuclidinol was added to the preformed substituted benzyl iodides and allowed to reflux at 90?°C for 15?h under nitrogen atmosphere. This method provides an efficient alternative of the preparation of amino benzyl ethers in organic synthesis with good yields in comparison with existed methods. |
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Keywords: | Amino benzyl ethers benzyl alcohols bicyclic amino alcohols nicotinic acetylcholine receptor Williamson reaction |
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