Carbazole → 1-(3-Carbazolyl)-3-(1-acetylpiperidin-4-yl)-1-propanone

HRID 260296

反応式

HRID 260296 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C)([O-])=O>[CH:10]1[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[C:8]([C:25](=[O:26])[CH2:24][CH2:23][CH:20]2[CH2:21][CH2:22][N:17]([C:14](=[O:16])[CH3:15])[CH2:18][CH2:19]2)[CH:9]=1

参加物

5

反応物 3

HCID 6854CarbazoleHCID 6451240Aluminum(III) ChlorideHCID 104659513-(1-Acetyl-4-piperidinyl)propionyl chloride

生成物 1

HCID 214767121-(3-Carbazolyl)-3-(1-acetylpiperidin-4-yl)-1-propanone収率 25%

試薬・触媒・溶媒 1

HCID 6375Nitromethane溶媒

反応条件

温度
70 °C

実験手順

To a 90 ml solution of 5.0 g of carbazole and 7.2 g of 3-(1-acetylpiperidin-4-yl)propionyl chloride in nitromethane, 9.3 g of aluminum chloride was added little by little, followed by stirring at 70° C. for 11 hours. The reaction mixture was poured over 100 ml of ice water, and the organic layer was separated and then washed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water. After the mixture was dried over anhydrous sodium sulfate, the solvent was distilled off to yield an oily residue. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-methanol=20:1 (v/v)) to yield 2.6 g of the title compound as a light yellow powder.

後処理

  1. customthe organic layer was separated
  2. washwashed by sequential additions of a 50 ml saturated aqueous sodium hydrogen carbonate solution and 50 ml of distilled water
  3. dry with materialAfter the mixture was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customto yield an oily residue
  6. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-methanol=20:1 (v/v))

出典と根拠

ORDレコード
ord-d0e0290264c64ebfb3fed5b936f94e58
出典データセット
uspto-grants-1996_06
特許番号
US05527800

関連ノート

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