تفاعل #10264

معادلة التفاعل

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

المردود 85.8%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر