反应 #2557

反应方程式

sodium cyanoborohydride

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

hydrochloric acid

sodium carbonate

o-anisidine

→

title compound

收率 66.2%

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

收率 66.2%

溶剂

methanol

THF

反应条件

后处理

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

实验过程

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.

来源