Hydrochloric Acid → 2,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)

HRID 1668596Notes

Reaction equation

HRID 1668596 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][C:4](=O)[NH:3][C:2]1=O.CO.[ClH:16]>C(OCC)C>[ClH:16].[CH2:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:1][CH2:2][NH:3][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7405391H-3-benzazepine-2,4(3H,5H)-dione

Product 1

HCID 170652302,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)Yield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 1,5-dihydro-benzo[d]azepine-2,4-dione (9.3 g) in toluene (250 ml) borane-methylsulfide complex (20 ml) was added dropwise under nitrogen atmosphere, then the mixture was heated at reflux for 4 h. MeOH (20 ml) was added dropwise and the mixture refluxed for additional 1 h, then cooled to room temperature. A 10% solution of anidrous HCl in ethyl ether (50 ml) was added and the solid precipitate was filtered off, washed with ethyl ether and desiccated under reduced pressure to afford the title compound as a white solid (7.6 g, 78% yield).

Workup

  1. additionwas added dropwise under nitrogen atmosphere
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 4 h
  4. temperaturethe mixture refluxed for additional 1 h
  5. filtrationthe solid precipitate was filtered off
  6. washwashed with ethyl ether

Sources & evidence

ORD record
ord-90abf9a9ab5a46259508b58d628e8345
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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