Acetic Anhydride → HCID 21535060, compound

Participants

Reaction Steps

Two grams of 1-(2-methyl-4-acetamidophenoxy)-3-{N-[2-(4-acetamidophenoxy)ethyl]-N-benzylamino}propan-2-ol are added to 20 ml. of anhydrous pyridine, followed by the immediate addition of 8.0 g. of acetic anhydride to the mixture with stirring. The resulting solution is then refluxed for a period of five minutes, cooled and subsequently poured into 50 ml. of ice water. The latter aqueous soltuion is then basified with 2N aqueous sodium hydroxide solution and extracted with chloroform, and the chloroform extract is thereafter washed with water and dried over anhydrous sodium sulfate prior to concentration in vacuo. The crude product obtained in this manner is then recrystallized from ethanol to afford pure 1-(2-methyl-4-acetamidophenoxy)-3-{N-[2-(4-acetamidophenoxy)ethyl]-N-benzylamino}-2-acetoxypropane. On subsequent treatment with hydrogen in the presence of palladium-on-carbon, the latter compound then gave 1-(2-methyl-4-acetamidophenoxy)-3-[2-(4-acetamidophenoxy)ethylamino]-2-acetoxypropane.

Provenance & Evidence