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Boron trifluoride etherate → 10,11-dihydro-10-methoxycarbonylpropylimino-5H-dibenz[b,f]azepine-5-carboxamide

HRID 361323
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 361323
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1.Cl.[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][NH2:27].B(F)(F)F.CCOCC>C1(C)C(C)=CC=CC=1>[CH3:21][O:22][C:23]([CH2:24][CH2:25][CH2:26][N:27]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]([NH2:15])=[O:14])[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1)=[O:28]
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Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 34312OxcarbazepineHCID 27563834-Aminobutyric acid methyl ester hydrochloride

Produkt 1

HCID 5715571810,11-dihydro-10-methoxycarbonylpropylimino-5H-dibenz[b,f]azepine-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a suspension of 0.2 g (0.79 mmol) of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide and 0.1 g (0.67 mmol) of methyl-4-aminobutyrate hydrochloride in 5 mL of xylene was added 0.07 g (0.49 mmol) of boron trifluoride diethyl etherate. The resulting mixture was heated at 135° C. for seven hours and then allowed to cool to room temperature. The mixture was then filtered and the residue was extracted with toluene. The combined extracts were evaporated under reduced pressure and the residue chromatographed on silica gel using a 4:1 mixture of petroleum ether-ethyl acetate. Chromatographically homogenous fractions were pooled and the solvents were removed under reduced pressure to give the desired product as a yellow oil which crystallised on standing to give yellow crystals which decomposed on heating without melting.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was then filtered
  3. extractionthe residue was extracted with toluene
  4. customThe combined extracts were evaporated under reduced pressure
  5. customthe residue chromatographed on silica gel using
  6. additiona 4:1 mixture of petroleum ether-ethyl acetate
  7. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-711b24ff6bee4af983e5f51cecb84810
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05866566

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