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

HRID 2083992Notes

Reaction equation

HRID 2083992 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-ad22489288f842cc8bb7e78ab49c0df9
Source dataset
uspto-grants-2004_04
Patent number
US06716841B2

Reaction notes

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