Реакция #1713

Уравнение реакции

N-Carboxy-[1-butylpiperidin-4-ylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole

2,3-dichloro-5,6-dicyano-1, 4-benzoquinone

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

→

title compounds

N-Carboxy-[1-butyl-4-piperidinylmethyl]-carbazole

Растворители

chloroform

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux for 12 hours
3. 3
   Температураcooled
4. 4
   workup.STIRRINGwith stirring
5. 5
   ТемператураThe mixture was heated
6. 6
   Температураto reflux for 12 hours
7. 7
   Температураcooled
8. 8
   Другоеevaporated under reduced pressure
9. 9
   ДругоеThe residue was purified by Silica-gel chromatography
10. 10
    Промывкаeluting with 2%MeOH/CHCl3

Методика

N-Carboxy-[1-butylpiperidin-4-ylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole (0.530 g, 1.32 mmol) was dissolved in chloroform (25 ml) and treated with 2,3-dichloro-5,6-dicyano-1, 4-benzoquinone (0.329 g, 1.58 mmol) with stirring. The mixture was heated to reflux for 12 hours, cooled, and more 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.329 g 1.58 mmol) added with stirring. The mixture was heated to reflux for 12 hours, cooled and evaporated under reduced pressure. The residue was purified by Silica-gel chromatography, eluting with 2%MeOH/CHCl3 to give the title compounds as 3:1 mixture. The mixture was separated by preparative HPLC using a Waters Micro Bondapak C18 (300 mm×7.8 mm) column and eluting with 75:25 MeCN: 0.1M Ammonium Acetate (pH 5.0).

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