N-bromobutanimide → 7-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

HRID 1521574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521574
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].[Br:13]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:13][C:10]1[CH:9]=[CH:8][C:7]2[NH:1][C:2](=[O:12])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:11]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Produkt 1

HCID 149781117-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the title compound from Example 2 Step B (17.0 g, 106 mmol) in N,N-dimethylformamide (500 mL) was added N-bromosuccinimide (25.2 g, 141 mmol) at room temperature, and then the mixture was refluxed for 16 hours. The reaction mixture was diluted with ethyl acetate (1 L), and the separated organic layer was washed with 0.1 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography on silica gel (petroleum ether:ethyl acetate=12:1 to 3:1) provided a crude product that was recrystallized from ethyl acetate and petroleum ether (v:v=1:10) to give the title compound: LCMS m/z=241 [M+2+H]+. 1H NMR (400 MHz, d6-DMSO): δ 9.56 (s, 1H), 7.46 (s, 1H), 7.37 (d, J=8.4 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 2.65 (m, 2H), 2.12-2.07 (m, 4H).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 hours
  2. washthe separated organic layer was washed with 0.1 M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (petroleum ether:ethyl acetate=12:1 to 3:1)
  7. customprovided a crude product that
  8. customwas recrystallized from ethyl acetate and petroleum ether (v:v=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-d381ec2eff0d467891f37d4bd14e601f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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