반응 #10264

반응 방정식

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

수율 85.8%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도After cooling to room temperature the solvent
2. 2
   기타was removed in vacuo
3. 3
   workup.ADDITIONthe residue treated with dichloromethane and NaOH (2N)
4. 4
   기타The layers were separated
5. 5
   건조the organic layer was dried (Na2SO4)
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 97/3)

실험 절차

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).

출처