Water → Ethyl α-(p-Methoxyphenyl)-β-(dimethylamino)propionate

Participants

Reaction Steps

4.645 g (0.0186 mol) of ethyl α-(p-methoxyphenyl)-β-(dimethylamino)acrylate were dissolved in 225 ml of ethanol in a 1 liter glass reactor, 7,46 g of Pt/C type 18 catalyst were added (4.83% Pt and 59.70% water) and a pressure of 200 psi of H2 was applied. The mixture was left hydrogenating for 3 days, after which it was filtered through Celite® 535 and was washed with 2×40 ml of ethanol. The ethanol was then removed under vacuum, to give a residue weighing 0.72 g. The residue was suspended in 40 ml of 2N hydrochloric acid and was washed with dichloromethane. The operation continued with the acid aqueous phase which was basified with a mixture of sodium carbonate and potassium carbonate (1/1) to pH 11 and the product was extracted with 4×40 ml of dichloromethane. The pooled organic phases were dried with sodium sulfate, were filtered and were evaporated to dryness under vacuum, to give a pale yellow oil weighing 3.82 g corresponding to ethyl α-(p-methoxyphenyl)-β-(dimethylamino)propionate (Yield: 82%).

Provenance & Evidence