Acetyl chloride → 9-acetyl-6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615033
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:21]2[CH:20]=[CH:19][C:18]3[C:22](=[O:25])[CH2:23][CH2:24][C:17]=3[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2.[Al+3].[Cl-].[Cl-].[Cl-].[C:30](Cl)([CH3:32])=[O:31].C([O-])(O)=O.[Na+]>C1([N+]([O-])=O)C=CC=CC=1.O>[C:30]([C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:8][CH2:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])[C:21]3[CH:20]=[CH:19][C:18]4[C:22](=[O:25])[CH2:23][CH2:24][C:17]=4[C:16]=3[C:15]=2[CH:14]=1)(=[O:31])[CH3:32]

Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 585449036-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Produkt 1

HCID 453817279-acetyl-6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

Compound 65 (0.336 g, 1.00 mmol) was dissolved in PhNO2 (7 mL). The solution was cooled down in an ice bath. Then, AlCl3 (0.67 g, 5.02 mmol) and after that, AcCl (0.36 mL, 5.04 mmol) were added. The resulting mixture was kept for 40 min (LC/MS monitoring), diluted with water, neutralized with aqueous NaHCO3 solution, extracted with CHCl3, and evaporated. The product was purified on a short thick column, eluent: 100:0→90:10. Yield of product: 0.307 g (82%) (R); S-isomer was obtained similarly (77%).

Aufarbeitung

  1. temperatureThe solution was cooled down in an ice bath
  2. extractionextracted with CHCl3
  3. customevaporated
  4. customThe product was purified on a short thick column, eluent
  5. customS-isomer was obtained similarly (77%)

Quellen und Nachweise

ORD-Eintrag
ord-1812235560264ece838aa6ca42eb8818
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765738B2

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