O1CCOCC1.[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:17])[CH2:15][CH3:16])=[CH:10][CH:9]=1.[Br:18]Br.[CH2:20]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH3:16][CH:15]([N:30]1[CH2:31][CH2:32][CH:27]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:28][CH2:29]1)[CH:14]([OH:17])[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1.[BrH:18]To a mixture of 3 ml of dioxane and 1 ml of methanol 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 was introduced thereinto at a flow rate of 400 ml/minute for 15 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 11.4 g (70.4%) of ifenprodil hydrobromide were obtained as white crystals.
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