Реакция #10264

Уравнение реакции

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

Выход 85.8%

Растворители

acetonitrile

Условия реакции

Обработка

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

Методика

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).

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