N-bromobutanimide → HCID 22292777, Verbindung

HRID 221235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221235
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:21]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 22292800HCID 22292800, Verbindung

Produkt 1

HCID 22292777HCID 22292777, VerbindungAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.25 g, 4.35 mmol) in acetonitrile (40 mL) was treated with N-bromosuccinimide (0.852 g, 4.79 mmol) and stirred overnight at 20 C. The product mixture was diluted with EtOAc (200 mL), washed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.55 g of a clear oil. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.34 (s, 1 H), 6.65 (m, 1 H), 3.87 (s, 3H), 3.81 (m, 1 H), 3.55 (m, 1.3 H), 3.37 (m, 0.7 H), 3.2-2.9 (bm, 4 H), 1.30 (m, 3 H). MS calculated for C14H15BrF3NO2+H: 366, observed: 366.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6005865fa69f419191410ce6d20b36b1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207158B2

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