Реакция #2557

Уравнение реакции

sodium cyanoborohydride

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

hydrochloric acid

sodium carbonate

o-anisidine

→

title compound

Выход 66.2%

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

Выход 66.2%

Растворители

methanol

THF

Условия реакции

Обработка

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

Методика

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.

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