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

HRID 49275

Reaction equation

HRID 49275 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-3e963c5dde66409ea279c5adefe9eda1
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Linked notes

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