Recently, we developed a rapid procedure for the Leuckart reaction and successfully applied it for the synthesis of substituted N-benzyl-N-methylformamides. Interestingly, in the reaction conducted on 4-cyanobenzaldehyde, a large amount of a by-product, of 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%.<br/>We propose that due to the presence of a methyl group attached to the carbonyl, the reaction conducted on 4-cyanoacetophenone will proceed slower and produce a higher yield of N-[1-(4-cyanophenyl)ethyl]-N-methylformamide and a lower yield of N,N-di[1-(4-cyanophenyl)ethyl]-N-methylamine. The reaction was conducted on 10 mmol scale at 187-190° 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 completed in 40 minutes compared to 10 minutes for the reaction with 4-cyanobenzaldehyde. The isolated yield of N-[1-(4-cyanophenyl)ethyl]-N-methylformamide was 82.48%. N,N-di[1-(4-cyanophenyl)ethyl]-N-methylamine was not isolated or detected. The results of the reaction support the initial hypothesis. The reaction provides a new method for the synthesis of N-[1-(4-cyanophenyl)ethyl]-N-methylformamide

Rapid synthesis of N-[1-(4-cyanophenyl)ethyl]-N-methylformamide

ACS Spring 2022

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