2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Carboxy-[1-butyl-4-piperidinylmethyl]-carbazole

HRID 1617

Reaktionsgleichung

Reaktionsgleichung von HRID 1617
[C:1]([N:4]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH:15]2[CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)([OH:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)(Cl)Cl>[C:1]([N:4]1[C:16]2[C:15]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]3)=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)([OH:3])=[O:2]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 67817506N-Carboxy-[1-butyl-4-piperidinylmethyl]-1,2,3,4,4a,9a-hexahydrocarbazole

Produkt 1

HCID 19691861N-Carboxy-[1-butyl-4-piperidinylmethyl]-carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 hours
  3. temperaturecooled
  4. stirringwith stirring
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 12 hours
  7. temperaturecooled
  8. customevaporated under reduced pressure
  9. customThe residue was purified by Silica-gel chromatography
  10. washeluting with 2%MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-4f6016db03934931aac4c3c4d6a66417
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726187

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