86298-22-8Relevant articles and documents
N-methylation of NH-containing heterocycles with dimethyl carbonate catalyzed by TMEDA
Zhao, Sheng-Yin,Zhang, Hai-Quan,Zhang, Deng-Qing,Shao, Zhi-Yu
experimental part, p. 128 - 135 (2011/11/01)
A practical method for N-methylation of NH-containing heterocycles using an environmentally safe and less toxic methylating reagent, dimethyl carbonate, has been developed. N,N,N',N'-tetramethylethylenediamine (TMEDA), an extremely active organocatalyst for the methylation of imides, indoles, benzimidazoles, and piperazines in conjunction with dimethyl carbonate, can lead to N-methylation products with high conversion. The reaction sequence consists of competing alkylation and acylation pathways and involves TMEDA as a nucleophilic catalyst. A possible reaction mechanism is discussed based on the reaction results.