Réaction #2557

Équation de réaction

sodium cyanoborohydride

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

hydrochloric acid

sodium carbonate

o-anisidine

→

title compound

Rendement 66.2%

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

Rendement 66.2%

Solvants

methanol

THF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source