Pyridine → 3-Bromo-7-phenyl-hexahydroazepin-2-one

HRID 263484Notes

Reaction equation

HRID 263484 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]1([CH:13]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CC=CC=1.[Br-:27].[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C(Cl)Cl>[Br:27][CH:17]1[CH2:16][CH2:15][CH2:14][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:19][C:18]1=[O:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 105595527-Phenylazepan-2-oneHCID 86751012Phenyltrimethylammonium bromide tribromide

Product 1

HCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 250 ml round-bottomed flask equipped with N2 inlet were added 5.12 g (24.6 mmol) phosphorus pentachloride and 45 ml methylene chloride. To the stirring mixture cooled to 0° C. was added dropwise over 20 minutes, a solution of 4.65 g (24.6 mmol) 7-phenyl-hexahydroazepin-2-one and 3.98 ml (49.2 mmol) pyridine in 40 ml methylene chloride. To the stirring mixture at 0° C. was then added 9.25 g (24.6 mmol) phenyltrimethylammonium bromide tribromide. The reaction was then allowed to warm to room temperature and stirred for 3 hours. It was then evaporated, taken up in tetrahydrofuran, quenched with water, evaporated, and partitioned between water and methylene chloride. The organic layer was washed with water and saturated aqueous sodium bisulfite, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel with ethyl acetate/hexane as eluent to afford the product as an oil, 4.0 g (61%).

Workup

  1. customTo a 250 ml round-bottomed flask equipped with N2 inlet
  2. additionwas added dropwise over 20 minutes
  3. temperatureto warm to room temperature
  4. customIt was then evaporated
  5. customquenched with water
  6. customevaporated
  7. custompartitioned between water and methylene chloride
  8. washThe organic layer was washed with water and saturated aqueous sodium bisulfite
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe residue was chromatographed on silica gel with ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-8c3225f7c67c491a97ccf6afc04db946
Source dataset
uspto-grants-1997_07
Patent number
US05643904

Reaction notes

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