[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.BrBr.C([O-])(=O)C.[Na+].[CH2:19]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H][H]>[C].[Pd].CO.O1CCOCC1>[CH3:10][CH:9]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:27][CH2:28]1)[CH:8]([OH:11])[C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1To 5 ml of dioxane were added 3.0 g of 4'-hydroxypropiophenone. 3.6 Grams of bromine were added dropwise to the mixture with stirring at room temperature, and the reaction liquid was stirred for an additional 10 minutes. To the reaction liquid were then added 1.7 g of anhydrous sodium acetate, 3.7 g of 4-benzylpyridine and 40 ml of methanol, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 60 ml of methanol and 3.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was stirred for 8 hours at 90°-95° C. under pressure of 20 kg/cm2. The reaction mixture was then treated in the same manner as described in Example 18, whereby 4.7 g (61.0%) of ifenprodil were obtained as white crystals.
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