Methylamine → Methyl N-(3-methoxy-3-oxopropyl)-N-methyl-beta-alaninate

Participants

Reaction Steps

Into a 3 L round bottom flask cooled in a water bath and equipped with an overhead stirrer, thermometer, gas inlet tube and a solid carbon dioxide/acetone filled condensor under a nitrogen atmosphere were placed 4-methoxyphenol (Aldrich, 3.5 g) and methyl acrylate (Aldrich, 907 g, 10.5 mol). Methylamine (Aldrich, 163 g, 5.25 mol) was added slowly over about two hours through the gas inlet tube keeping the temperature less than about 30° C. After the addition was complete, the reaction mixture was stirred for 16 hours at ambient temperature. The excess methyl acrylate and much of the 1:1 addition product were then distilled from the reaction mixture under a vacuum of 3 mm Hg giving a final product purity of 96.6% the desired CH3N(CH2CH2CO2CH3)2.

Provenance & Evidence