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

HRID 2293444노트

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HRID 2293444 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6375Nitromethane용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-b07666e1600a4b04a5ebba839dbd1e33
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686466

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