반응 #653101

반응 방정식

1-(4-(3-bromocinnamoylamino)-benzyl)piperidine

4-fluorophenyl borate

potassium carbonate

ethanol

→

1-(4-(3-(4-fluoro-phenyl)cinnamoylamino)benzyl)piperidine

수율 92.8%

용매

toluene

반응 조건

후처리

1. 1
   온도the mixture was refluxed over night
2. 2
   추출The mixture was extracted with ethyl acetate
3. 3
   세척the organic layer was washed with water and saturated sodium chloride solution
4. 4
   건조dried with anhydrous magnesium sulfate
5. 5
   기타Under reduced pressure, the solvent was evaporated
6. 6
   기타the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate)
7. 7
   기타to give crude crystals, which
8. 8
   기타were recrystallized from ethyl acetate-hexane

실험 절차

A suspension of 1-(4-(3-bromocinnamoylamino)-benzyl)piperidine (0.4g), 4-fluorophenyl borate (0.14g), 1 M potassium carbonate (2ml) and ethanol (1ml) in toluene (5ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the suspension was added tetrakistriphenylphosphinepalladium (0.05g), and the mixture was refluxed over night. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 1-(4-(3-(4-fluoro-phenyl)cinnamoylamino)benzyl)piperidine (Compound 83) (0.35g) as colorless crystals.

출처