반응 #2557

반응 방정식

sodium cyanoborohydride

1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine

hydrochloric acid

sodium carbonate

o-anisidine

→

title compound

수율 66.2%

4-(4-Fluorobenzoyl)-1-[2-(2-methoxyanilino)ethyl]piperidine

수율 66.2%

용매

methanol

THF

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   기타the solvent was removed by evaporation
3. 3
   workup.DISTILLATIONthe resulting residue was subjected to azeotropic distillation
4. 4
   기타to obtain an orange glutinous material
5. 5
   기타at room temperature
6. 6
   workup.STIRRINGAfter 2 hours of stirring at the same temperature
7. 7
   추출extracted with ethyl acetate
8. 8
   세척washed with water and saturated brine
9. 9
   건조The resulting organic layer was dried on anhydrous sodium carbonate
10. 10
    기타the solvent was removed by evaporation
11. 11
    기타the resulting residue was purified

실험 절차

1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine (81 mg, 0.25 mmol) was dissolved in THF (3 ml) to which was subsequently added 10% hydrochloric acid (2 ml) at room temperature. After 1 hour of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (5 ml×4) to obtain an orange glutinous material. The thus obtained residue was dissolved in methanol (2 ml) to which were subsequently added o-anisidine (29 μl, 0.25 mmol) and sodium cyanoborohydride (11 mg, 0.166 mmol) at room temperature. After 2 hours of stirring at the same temperature, the reaction solution was mixed with saturated sodium carbonate aqueous solution (10 ml), extracted with ethyl acetate and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=2:1-ether) to obtain 59 mg (66.2%) of the title compound in the form of colorless solid.

출처