Background: Recently, we developed a rapid procedure for the synthesis of substituted N-benzyl-N-methylformamides. Interestingly, in the reaction conducted on 4-cyanobenzaldehyde, a large amount of a by-product, N,N-di-(4-cyanobenzyl)-N-methylamine was produced with an isolated yield of 37.5%. N-(4-cyanobenzyl)-N-methylformamide was produced with an isolated yield of 46.5%. Hypothesis: Increasing the molar ratio of 4-cyanobenzaldehyde to N-methylformamide (from 1:50 to 1:5) should produce a higher yield of the respective dibenzyl product and a lower yield of the respective monobenzyl product. Methods: The reaction was conducted on a 10 mmol scale at 188-190 C. Column chromatography was used for the isolation of the products. NMR-spectroscopy and elemental analysis were used to determine the structures of the products. Results: The reaction was completed in 10 minutes. The isolated yields of N,N-di-(4-cyanobenzyl)-N-methylamine and N-(4-cyanobenzyl)-N-methylformamide were 66.5% and 31.6%, respectively. The ratio of the yield of the dibenzyl product to the yield of the monobenzyl product shifted from 1:1.24 to 2.10:1. Conclusions: The results of the reaction support the initial hypothesis. The reaction provides a new method for the synthesis of N,N-di-(4-cyanobenzyl)-N-methylamine.

Rapid synthesis of N,N-di-(4-cyanobenzyl)-N-methylamine

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.