4'-Hydroxypropiophenone → Ifenprodil hydrobromide

Participants

Reaction Steps

To 4 ml of dioxane were added 6.0 g of 4'-hydroxypropiophenone. 6.4 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 7.5 g of 4-benzylpyridine, 100 ml of methanol, and 2.8 ml of 10 N potassium hydroxide solution, and the mixture was refluxed under heating for 5 hours. After replacing the air in the reaction container with nitrogen gas, 3.0 g of 10% palladium-carbon were added and hydrogen was then introduced and the mixture was stirred for 8 hours at 60°-70° C. under pressure of 50 kg/cm2. The reaction mixture was then treated in the same manner as described in Example 26, whereby 12.1 g (74.4%) of ifenprodil hydrobromide were obtained as white crystals.

Provenance & Evidence