反应详情

温度

50 °C

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (2.73 g, 6.06 mmol) and 1-naphthalen-2-yl-piperazine (3.86 g, 18.2 mmol) in anhydrous dimethylsulfoxide (60 mL) was heated at 50° C. overnight. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (300 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography on silica gel (2/2/95 methanol/ammonium hydroxide/methylene chloride) did not provide clean product. Re-chromatography on silica gel (90/5/5 ethyl acetate/hexane/triethylamine) afforded 1.80 g (69%) of the title compound as a beige solid: mg 134–137° C.; MS (ES) m/z426 [M+H]+.

1. customThe cooled reaction
2. extractionextracted with ethyl acetate (3×200 mL)
3. washThe combined organic layers were washed with brine (300 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customFlash chromatography on silica gel (2/2/95 methanol/ammonium hydroxide/methylene chloride) did not provide clean product