反应详情

温度

110 °C

3-Fluoropiperidine hydrochloride (106 mg, 0.76 mol) was dissolved in sodium hydroxide (1 M, 10 mL) and extracted with dichloromethane (4×10 mL), the combined extracts were dried over sodium sulfate, filtered and evaporated. Pyridine (2 mL) was added, followed by 1-cyano-4-fluoronaphthalene (108 mg, 0.63 mmol) and the vial was shaken at 110° C. overnight. GC-MS and TLC showed only very little conversion. DBU (10 μL) was added and the shaking was continued for 2 weeks at 110° C., after which GC-MS showed ˜50% conversion. The reaction was worked up in the same way as 165RL60 and purified by silica gel column chromatography eluted with a stepwise gradient of 0-60% ethyl acetate in n-heptane to give the title compound (29.3 mg, 12%) as a solid.

1. extractionextracted with dichloromethane (4×10 mL)
2. dry with materialthe combined extracts were dried over sodium sulfate
3. filtrationfiltered
4. customevaporated
5. additionPyridine (2 mL) was added
6. waitthe shaking was continued for 2 weeks at 110° C.
7. custompurified by silica gel column chromatography
8. washeluted with a stepwise gradient of 0-60% ethyl acetate in n-heptane