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

HRID 1617

反応式

HRID 1617 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f6016db03934931aac4c3c4d6a66417
出典データセット
uspto-grants-1998_03
特許番号
US05726187

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