反応 #77297

反応方程式

NaOH

2,4,5-trifluoroaniline

bis(2-chloroethyl)amine hydrochloride

sodium carbonate

→

title compound

収率 24.0%

(2,4,5-Trifluorophenyl)piperazine

収率 24.0%

溶媒

hexane

butanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 24 hours
3. 3
   温度the mixture was heated again
4. 4
   温度at reflux
5. 5
   温度the mixture was cooled to room temperature
6. 6
   その他the resulting layers were separated
7. 7
   抽出The aqueous layer was extracted with chloroform (3×25 mL)
8. 8
   洗浄The silica gel was further eluted with a gradient of chloroform to chloroform/methanol (4:1)
9. 9
   その他The solvent was removed from the combined fractions with Rf=0.20 [silica gel, chloroform/methanol (4:1)]

実験手順

A mixture of 2,4,5-trifluoroaniline (2.94 g, 20 mmol) and bis(2-chloroethyl)amine hydrochloride (3.56 g, 20 mmol) in butanol (10 mL) was heated at reflux for 24 hours. The mixture was cooled to room temperature, sodium carbonate (2.33 g, 22 mmol) was added, and the mixture was heated again at reflux. After 2 days, the mixture was cooled to room temperature, hexane (15 mL) and 3 N NaOH (25 mL) were added, and the resulting layers were separated. The aqueous layer was extracted with chloroform (3×25 mL) and the combined organic fractions were flashed over a column of silica gel. The silica gel was further eluted with a gradient of chloroform to chloroform/methanol (4:1). The solvent was removed from the combined fractions with Rf=0.20 [silica gel, chloroform/methanol (4:1)], giving the title compound as a yellow oil (1.028 g, 4.76 mmol, 24%). ESI-MS m/z 217 (MH+).

出典