反应详情

A mixture of 0.112 gm (0.7 mMol) 3-chloropropyl phenyl ether, 0.150 gm (0.7 mMol) 4-hydroxy-4-(quinolin-3-yl)piperidine, and 0.136 gm (1.5 mMol) potassium carbonate in 5 mL acetonitrile was heated to reflux for 18 hours. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase extracted well with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 25:2 dichloromethane:methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.142 gm (60%) of 1-(3-phenoxyprop-1-yl)-4-hydroxy-4-(quinolin-3-yl)piperidine as a light yellow, viscous oil. The oil was converted to the oxalate salt to provide the title compound.

1. temperaturewas heated
2. temperatureto reflux for 18 hours
3. custompartitioned between ethyl acetate and 2N sodium hydroxide
4. customThe phases were separated
5. extractionthe aqueous phase extracted well with ethyl acetate
6. washThe combined organic extracts were washed with saturated aqueous sodium chloride
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. washeluting with 25:2 dichloromethane
10. additionFractions containing product
11. concentrationconcentrated under reduced pressure