HCID 369399, compound → 7-Bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine hydrochloride

HRID 2301953Notes

Reaction equation

HRID 2301953 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:21][C:20](=O)[CH2:19][CH2:18][C:17](=O)[C:16]=2[CH:24]=1>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:24]=1

Participants

5

Reactant 3

HCID 369399HCID 369399, compoundHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 121488297-Bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine hydrochlorideYield 35.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of LAH (0.14 g, 3.69 mmol) in 10 mL of THF was added AlCl3 (0.46 g, 3.45 mmol) in two portions. The mixture was stirred at rt for 15 minutes and a solution of 7-bromo-3,4-dihydro-1H-1-benzazepine-2,5-dione (0.22 g, 0.87 mmol) in 10 mL of THF was added dropwwase. The mixture was then heated at 60° C. for 12 h. The reaction was cooled and quenched. It was extracted with EtOAc. The organic solution was washed with brine, dried over MgSO4, concentrated, and chromatographed with 20-100% EtOAc in hexane to give 0.07 g of 7-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine. MS (AP+): 267, 269, M+H.

Workup

  1. temperatureThe mixture was then heated at 60° C. for 12 h
  2. temperatureThe reaction was cooled
  3. customquenched
  4. extractionIt was extracted with EtOAc
  5. washThe organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed with 20-100% EtOAc in hexane

Sources & evidence

ORD record
ord-e4c42fa75ea34b2183fa99ad70356a40
Source dataset
uspto-grants-2002_08
Patent number
US06429205B1

Reaction notes

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