Reaktion #2557

Reaktionsgleichung

sodium cyanoborohydride

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

hydrochloric acid

sodium carbonate

o-anisidine

→

title compound

Ausbeute 66.2%

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

Ausbeute 66.2%

Lösungsmittel

methanol

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle