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Ethyl Acetate → 3-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2,a]azepin-2-yl)propyl carbamate

HRID 2379443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2379443
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[CH2:10]1[CH:15]2[C:16]3[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=3[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]2[CH2:13][CH2:12][N:11]1[CH2:29][CH2:30][CH2:31][OH:32].C(OCC)(=O)C>C(Cl)Cl>[C:3](=[O:4])([O:32][CH2:31][CH2:30][CH2:29][N:11]1[CH2:12][CH2:13][N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][C:17]3[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=3[CH:15]2[CH2:10]1)[NH2:5]
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Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 76400Trichloroacetyl isocyanateHCID 18999734HCID 18999734, Verbindung

Produkt 1

HCID 189997193-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2,a]azepin-2-yl)propyl carbamateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.2 ml of trichloroacetyl isocyanate were added to a solution of 400 mg of 3-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)propanol (prepared as described in Example 16) in 20 ml of methylene chloride, whilst ice-cooling, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in 22 ml of methanol, 9.0 g of silica gel were added to the solution and the mixture was stirred at room temperature for 15 hours. At the end of this time, the mixture was filtered using a Celite (trade mark) filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel eluted with ethyl acetate, to give, after recrystallization from ethyl acetate, 260 mg (yield 59%) of the title compound as crystals, melting at 160°-161° C.

Aufarbeitung

  1. temperaturecooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 22 ml of methanol
  4. addition9.0 g of silica gel were added to the solution
  5. stirringthe mixture was stirred at room temperature for 15 hours
  6. filtrationAt the end of this time, the mixture was filtered
  7. filtrationfilter aid
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. washeluted with ethyl acetate
  10. customto give

Quellen und Nachweise

ORD-Eintrag
ord-f80e2476e8ba4686a26c52afaff47da0
Quelldatensatz
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05362725

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