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

HRID 1617

Reaction equation

HRID 1617 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4f6016db03934931aac4c3c4d6a66417
Source dataset
uspto-grants-1998_03
Patent number
US05726187

Linked notes

Loading…