反応 #78239

反応方程式

sodium bicarbonate

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

4-n-butoxyaniline

Phosphorous oxychloride

→

titled compound

収率 24.0%

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

収率 24.0%

溶媒

methylene chloride

pyridine

反応条件

後処理

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

実験手順

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).

出典