N,N-Dimethyl-2-(p-tolyloxy)ethanamine

106-44-5

4584-46-7

51344-14-0

General procedure for the synthesis of N,N-dimethyl-2-(p-toluyloxy)ethylamine from p-methylphenol and dimethylaminochloroethane hydrochloride: 108 g (1 mol) of p-methylphenol, 61.7 g (1.1 mol) of potassium hydroxide, 200 mL of DMF, and 200 mL of isopropyl ether were added to the reactor. Subsequently 110 g (1.1 mol) of 2-(dimethylamino)chloroethane hydrochloride and 110 g of triethylamine were added. The mixture was stirred and reacted at 80°C for 2 hours. After completion of the reaction, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure to recover most of the solvent. The pH of the concentrate was adjusted to 2 with 2 mol-L-1 sulfuric acid and then extracted with 500 mL of chloroform in two portions. The aqueous phase was cooled in ice water, neutralized with 20% sodium hydroxide solution to pH 10, and then extracted with 500 mL ethyl acetate. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to recover the ethyl acetate. Finally, 162.8 g of N,N-dimethyl-2-(p-toluyloxy)ethylamine as a colorless oil was obtained by distillation in 91% yield.