反应详情

温度

80 °C

A solution of 4-(4-chlorophenyl)-4-fluoropiperidine hydrochloride (100 mg, 0.40 mmol) and 3,3-diphenyl-1-iodopropane (145 mg, 0.45 mmol) in DMF (2.5 mL) was treated with potassium carbonate (560 mg, 4.05 mmol) and the resulting suspension heated at 80° C. for 14 hours. After this time the reaction was cooled to room temperature and quenched by pouring into 25% aqueous ammonium chloride solution (20 mL). The resulting suspension was then extracted with ethyl acetate (2×10 mL) and the combined extracts washed with water (10 mL) and brine (10 mL) then dried over magnesium sulfate. Subsequent filtration and concentration under reduced pressure afforded crude 4-(4-chlorophenyl)-1-(3,3-diphenyl-propyl)-4-fluoropiperidine as a yellow oil. This material was treated with 10% methanolic hydrogen chloride (10 mL) and the solution concentrated under reduced pressure. Trituration of the resulting oil with 1:1 ethyl acetate/2-butanone (10 mL) afforded a solid which was isolated by filtration and vacuum dried. This afforded a 41% yield of 4-(4-chlorophenyl)-1-(3,3-diphenylpropyl)-4-fluoropiperidine hydrochloride as an off-white solid.

1. temperatureAfter this time the reaction was cooled to room temperature
2. customquenched
3. additionby pouring into 25% aqueous ammonium chloride solution (20 mL)
4. extractionThe resulting suspension was then extracted with ethyl acetate (2×10 mL)
5. washthe combined extracts washed with water (10 mL) and brine (10 mL)
6. dry with materialthen dried over magnesium sulfate
7. filtrationSubsequent filtration and concentration under reduced pressure