反应详情

Sodium (0.1 g, 4.35 mmol) in liquid ammonia (100-150 cm3) was stirred until the blue colour was discharged. A bomb was charged with [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.83 g, 2.93 mmol) and the liquid ammonia solution was added. The mixture was stirred at room temperature for 2 days then the bomb was cooled to -78° C., and ethyl picolinate (0.6 g, 3.97 mmol) was added. Stirring was continued for 3 hours at room temperature then the ammonia was allowed to evaporate and the gummy residue triturated with water then ethyl acetate. The ethyl acetate suspension was filtered to give recovered [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.33 g). The filtrate was evaporated and the residue chromatographed on silica eluting with chloroform then chloroform: ethyl acetate 4:1 to give the title compound (0.37 g).

1. temperaturethe bomb was cooled to -78° C.
2. stirringStirring
3. waitwas continued for 3 hours at room temperature
4. customto evaporate
5. customthe gummy residue triturated with water
6. filtrationThe ethyl acetate suspension was filtered
7. customto give
8. customrecovered [1-(naphth-2-ylmethyl)piperid-4-yl]urea (0.33 g)
9. customThe filtrate was evaporated
10. customthe residue chromatographed on silica eluting with chloroform