反应详情

温度

0 °C

1.4M Methyl Lithium in diethyl ether was added to a dry flask then cooled to 0° C. A solution of 4-[4-(2-Benzylamino-ethyl)-phenoxy]-benzonitrile (2.5 g, 7.6 mmol) (see example 4) in dry tetrahydrofuran (25 mL) was added dropwise to the reaction then stirred at 0° C. for 60 minutes. 3M Sulfuric Acid (12.7 mL, 38 mmol) was added dropwise then the reaction was heated at 50° C. for 3 hours. The reaction was cooled to room temperature then poured into saturated aqueous sodium bicarbonate solution then extracted with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 3.1 g of crude product, which was purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane to yield 1-{4-[4-(2-Benzylamino-ethyl)-phenoxy]-phenyl}-ethanone (0.6 g) which was used directly in the next step.

1. temperaturethe reaction was heated at 50° C. for 3 hours
2. temperatureThe reaction was cooled to room temperature
3. extractionthen extracted with dichloromethane (3×75 mL)
4. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated on a rotary evaporator
7. customto yield 3.1 g of crude product, which
8. customwas purified by flash column chromatography on silica gel eluting with ethanol in dichloromethane