Direct Synthesis of N,N-Dimethylated and beta-Methyl N,N-Dimethylated Amines from Nitriles Using Methanol: Experimental and Computational Studies

Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as Cl building blocks is reported using an air-and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug avil. Several kinetic experiments and detailed DFT understand the mechanism of this process.