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

HRID 905298Notes

Reaction equation

HRID 905298 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]=1

Participants

3

Reactant 2

HCID 127460203',4'-Bis(acetoxy)-2-bromoacetophenoneHCID 12876177N-[2-(benzylamino)ethyl]-2-phenylacetamide

Product 1

HCID 204467762-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(acetoxy)acetophenone

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.

Sources & evidence

ORD record
ord-3556c4d84089442d906597cfb047b627
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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