反応 #10264

反応方程式

phenacyl bromide

(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

potassium iodide

diisopropyl-ethylamine

→

(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(2-phenyl-2-ethanon-1-yl)piperazine

収率 85.8%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度After cooling to room temperature the solvent
2. 2
   その他was removed in vacuo
3. 3
   workup.ADDITIONthe residue treated with dichloromethane and NaOH (2N)
4. 4
   その他The layers were separated
5. 5
   乾燥the organic layer was dried (Na2SO4)
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 97/3)

実験手順

A mixture of phenacyl bromide (0.88 g), (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (2 g), potassium iodide (catalytical), diisopropyl-ethylamine (0.77 mL), and acetonitrile (20 mL) was stirred at room temperature overnight. After cooling to room temperature the solvent was removed in vacuo, and the residue treated with dichloromethane and NaOH (2N). The layers were separated, the organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 97/3) to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(2-phenyl-2-ethanon-1-yl)piperazine 2.16 g (85%). MH+ 574, Rf 0.44 (CH2Cl2/MeOH 97/3).

出典