4-Bromoaniline → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(4-bromophenyl)acetamide Hydrochloride

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Reaction Steps

500 mg (2.43 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid are dissolved in 10 ml of dichloromethane. At 0° C., 1.79 g (9.72 mmol) of pentafluorophenol and 699 mg (3.65 mmol) of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are added. Stirring at room temperature for 14 h is followed by concentration in vacuo, dissolving of the residue in 8 ml of dimethylformamide, addition of 627 mg (3.65 mmol) of p-bromoaniline and stirring further at room temperature for 14 h. 10 ml of 10% strength sodium bicarbonate solution and 10 ml of ethyl acetate are slowly added. The resulting precipitate is filtered off with suction, and the filtrate is extracted three times with ethyl acetate. After drying over sodium sulfate, concentration results in a precipitate, which is filtered off. The solid is suspended in dioxane, mixed with 4M HCl in dioxane and stirred at room temperature for 30 minutes. Renewed filtration of the solid with suction results in 621 mg (71% of theory) of the title compound in the form of white crystals.

Provenance & Evidence