3',4'-Bis(acetoxy)-2-bromoacetophenone → 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(acetoxy)acetophenone

Participants

Reaction Steps

3',4'-Bis(acetoxy)-2-bromoacetophenone was reacted with N-[2-(benzylamino)ethyl]-2-phenylacetamide using a similar procedure to that described in Example 1 for the analogous pivaloyloxy derivative to give 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(acetoxy)acetophenone, which was isolated as its free base and converted to its hydrochloride salt with ethereal hydrogen chloride to give a solid, m.p. 140°-145° C. This hydrochloride salt was dissolved in methanol containing 2% v/v of hydrobromic acid, and the solution was heated under reflux for 2 hours. After cooling to room temperature, the solution was diluted with ether (100 ml.) and stored at 0°-5° C. to give 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-dihydroxyacetophenone hydrobromide as a white solid in 98% yield, m.p. 175°-177° C. (after recrystallisation from methanol/ether).

Provenance & Evidence