3',4'-Bis(acetoxy)-2-bromoacetophenone → 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(acetoxy)acetophenone
Reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:15](=[O:18])[CH2:16]Br)[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].[CH2:19]([NH:26][CH2:27][CH2:28][NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]([CH2:16][C:15]([C:7]1[CH:8]=[CH:9][C:10]([O:11][C:12](=[O:14])[CH3:13])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=1)=[O:18])[CH2:27][CH2:28][NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-979280ff55504e8eafd1e2eb68c1ac36
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04470997
Reaction notes
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