C(O)C.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1.[Br:15]Br.[CH2:17]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:13][CH:12]([N:27]1[CH2:28][CH2:29][CH:24]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:25][CH2:26]1)[CH:11]([OH:14])[C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1.[BrH:15]To 5 ml of ethanol were added 6.0 g of 4'-hydroxypropiophenone. 6.4 Grams of bromine were added dropwise to the mixture with stirring at room temperature. The reaction liquid was stirred for an additional 10 minutes and then nitrogen gas was introduced thereinto at a flow rate of 100 ml/minute for 30 minutes at 60° C. To the reaction liquid were then added 7.5 g of 4-benzylpyridine and 100 ml of methanol, and the mixture was refluxed under heating for 5 hours. The reaction mixture was then treated in the same manner as described in Example 5, whereby 10.2 g (62.7%) of ifenprodil hydrobromide were obtained as white crystals.
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