Sodium hydride → 6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 514783

Reaktionsgleichung

Reaktionsgleichung von HRID 514783
[CH2:1]1[C:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:3](=[O:17])[CH2:2]1.[H-].[Na+].Cl.Cl[CH2:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29].C(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[CH3:29][N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[CH2:23][CH2:22][N:8]1[C:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:17])[CH2:2][CH2:1][C:16]=3[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 21584188Chloroform methanolHCID 58544896HCID 58544896, Verbindung

Produkt 1

HCID 585449036-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Carbazole 46 (0.4 g, 1.81 mmol) was dissolved in CH2Cl2 (7 mL), then NaH (0.22 g, 5.50 mmol) was added. The mixture was stirred at room temperature for 5-10 min, and 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (0.4 g, 2.17 mmol) was added. The mixture was heated to 60° C. and kept at this temperature for 4 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1). The resulting mixture was poured into water. The product was extracted with ethyl acetate, dried over Na2SO4, and evaporated. The residue was triturated with ether. The precipitate was filtered off. Yield of 65: 0.365 g (61%)—S-isomer and 0.336 g (55%)—R-isomer.

Aufarbeitung

  1. temperatureThe mixture was heated to 60° C.
  2. waitkept at this temperature for 4 h
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was triturated with ether
  7. filtrationThe precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-6386de38e7034ad98a8451b6cdda36dc
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108916B2

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