Synthesis of N-Methylmorpholine from Morpholine and Dimethyl Carbonate

Abstract

The synthesis of N-methylmorpholine from morpholine and dimethyl carbonate was investigated. The effects of reaction variables upon the formation of the compounds were also examined. Under the optimized conditions, higher yield of N-methylmorpholine 83 % was obtained and the selectivity of N-methylmorpholine was 86 %. The mechanism on formation of product and undesired product was proposed based on the experimental results.

Unveiling the mechanism of N‐methylation of indole with dimethylcarbonate using either DABCO or DBU as catalyst

“…N ‐Methylation of indoles, 18,22 imidazoles, 22,23 and morpholines 24,25 with DMC are well documented, 15 and different nucleophilic amines, such as N , N ‐dimethylpyridin‐4‐amine (DMAP), 26 N , N , N ′, N ′‐tetramethylethylenediamine (TMEDA), 27 and 2,4‐diaminotoluene, have been used as organocatalysts. Phase‐transfer catalysts have also been employed 28 …”

“…[15][16][17][18][19][20][21] DMC synthesis (Scheme 1) also employs an eco-friendly oxidative carbonylation of methanol with oxygen. 16 N-Methylation of indoles, 18,22 imidazoles, 22,23 and morpholines 24,25 with DMC are well documented, 15 and different nucleophilic amines, such as N,N-dimethylpyridin-4-amine (DMAP), 26 N,N,N 0 ,N 0 -tetramethylethylenediamine (TMEDA), 27 and 2,4-diaminotoluene, have been used as organocatalysts. Phasetransfer catalysts have also been employed.…”