Recently, we developed a rapid procedure for the synthesis of substituted N-benzyl-N-methylformamides. Interestingly, in the reaction conducted on piperonal (3,4-methylenedioxybenzaldehyde), a large amount of a by-product, N-methyl-N,N-dipiperonylamine was produced with an isolated yield of 32.8%. N-methyl-N-piperonylformamide was produced as the main product with an isolated yield of 51.4%. We hypothesized that the reaction conducted on electron-donating aromatic aldehydes may produce higher yields of N,N-diaryl-N-methylamines and lower yields of N-aryl-N-methylformamides. In this work the hypothesis was tested by conducting the reaction on 3-indolecarboxaldehyde. The reaction was conducted on 10 mmol scale at 183 °C. Column chromatography was used for the isolation of the products of the reaction. NMR-spectroscopy and elemental analysis were used to determine the structures of the products. The reaction was fully completed in 10 minutes. Currently, N-(3-indolylmethyl)-N-methylformamide is the only isolated product with a yield of 39.8%. Work on isolating N,N-di-(3-indolylmethyl)-N-methylamine is underway. The reaction comprises a new rapid method for the synthesis of N-(3-indolylmethyl)-N-methylformamide. Research reported in this publication was supported by an Institutional Development Award (IDeA) from the National Institute of General Medical Sciences of the National Institutes of Health under grant number P20GM103442.

Rapid synthesis of N-(3-indolylmethyl)-N-methylformamide

251st National Meeting (2016)

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