The reductive amination reaction between an amine and an aldehyde or ketone is an important method to add an additional alkyl group to an amine nitrogen. In this experiment, students react a selection of benzylamines with aldehydes to form the corresponding imines. These imines are reduced with a mixture of p -toluenesulfonic acid monohydrate and sodium borohydride to afford dibenzylamines in good yields. Comparison of the melting points of the hydrochloride salts with a set of known melting points is used identify the amine–aldehyde coupling partners. Formation of the product is also confirmed using NMR spectroscopy.
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Goldstein et al. (2015) studied this question.
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