반응 #167497

반응 방정식

Compound 24

[diphenyl(4-methylphenyl)]methanol

thionyl chloride

piperidine

→

title compound

수율 85.0%

[[diphenyl(4-methylphenyl)]methyl]piperidine

수율 85.0%

용매

chloroform

acetonitrile

반응 조건

후처리

1. 1
   온도while cooling with ice
2. 2
   기타was returned to room temperature
3. 3
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
4. 4
   기타to thereby obtain a residue
5. 5
   온도The mixture was refluxed for 1 hour
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   workup.ADDITIONa saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture
8. 8
   추출was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
9. 9
   세척The organic layer was washed with water and brine
10. 10
    건조After that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
11. 11
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

실험 절차

Compound 24 described above (0.17 g, 0.620 mmol) was dissolved in chloroform (4 mL) (Wako Pure Chemical Industries, Ltd.), and thionyl chloride (0.5 mL) (Wako Pure Chemical Industries, Ltd.) was added dropwise while cooling with ice. The mixture was returned to room temperature and stirred for 2 hours, and then the solvent was distilled off under reduced pressure, to thereby obtain a residue. The residue was dissolved in acetonitrile (4 mL) (Wako Pure Chemical Industries, Ltd.), and piperidine (0.19 g, 2.23 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto. The mixture was refluxed for 1 hour and allowed to cool to room temperature. The solvent was distilled off under reduced pressure, and then a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the concentrated residue, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was washed with water and brine. After that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to alumina column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.18 g, 85% yield).

출처