Water → 1,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

HRID 49275

Reaktionsgleichung

Reaktionsgleichung von HRID 49275
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH2:7][CH2:6][CH2:5][N:4]([C:9]3[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=3)[CH2:3][CH2:2]2)=[N:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 693532,5-Dibromopyridine

Produkt 1

HCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of hexahydro-1,4-diazepine (2.84 g, 28.4 mmol) in dimethylformamide (14 mL) were added 2,5-dibromopyridine (16.23 g, 68.5 mmol) and potassium carbonate powdered in a mortar (8.00 g, 57.9 mmol), and the resultant mixture was stirred at 120° for 15 hours. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield crude crystals of the title compound (7.67 g, yield: 66%). The crude crystals were recrystallized from chloroform-hexane to give colorless fine needles (melting point: 178.0-181.0° C.).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3e963c5dde66409ea279c5adefe9eda1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706703B2

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