반응 #78239

반응 방정식

sodium bicarbonate

(1-benzyl-4-hydroxypiperidin-4-yl) acetic acid lithium salt

4-n-butoxyaniline

Phosphorous oxychloride

→

titled compound

수율 24.0%

N-(4-n-butoxyphenyl)-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide

수율 24.0%

용매

methylene chloride

pyridine

반응 조건

후처리

1. 1
   추출the solution was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with water and saturated brine
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   기타The residue was purified with silica gel column chromatography (elution solvent; methylene chloride:methanol=19:1 to 9:1)

실험 절차

To a solution of (1-benzyl-4-hydroxypiperidin-4-yl) acetic acid lithium salt (3.09 g) in methylene chloride (60 mL) were added 4-n-butoxyaniline (2.0 g) and pyridine (2.14 mL). Phosphorous oxychloride (1.19 mL) was added dropwise to the solution under cooling with an ice-sodium chloride, followed by stirring at 5 to 10° C. for 1 hour. The mixture was made alkaline with saturated aqueous sodium bicarbonate under cooling with an ice-water, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography (elution solvent; methylene chloride:methanol=19:1 to 9:1) to obtain the titled compound (1.15 g).

출처