7-Bromo-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one → 7-Bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine hydrochloride

HRID 631849Notes

Reaction equation

Br[C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][C:7](=O)[NH:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[Br:14]C1C=CC2CNC(=O)CCC=2C=1>O1CCCC1>[Br:14][C:12]1[CH:5]=[CH:6][C:7]2[NH:8][CH2:9][CH2:10][CH2:4][CH2:3][C:2]=2[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 1000-mL round-bottom flask was added the mixture of 7-bromo-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 7-bromo-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one (12.6 g, 52 4 mmol) and tetrahydrofuran (260 mL). The solution was cooled to 0° C. and borane-methylsulfide complex (12.4 mL, 210 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 10 min, warmed to room temperature and stirred for 3 h, then heated at reflux for 4 h. Upon cooling to room temperature, the mixture was quenched with MeOH (50 mL) to remove excess borane. The solvent was then evaporated to give 7-bromo-2,3,4,5-tetrahydro-1H-benzoazepine and 7-bromo-2,3,4,5-tetrahydro-1H-benzoazepine as sticky oil. LCMS: (FA) ES+226 and 228.

Workup

additionTo a 1000-mL round-bottom flask was added
additionborane-methylsulfide complex (12.4 mL, 210 mmol) was slowly added
temperaturewarmed to room temperature
stirringstirred for 3 h
temperatureheated
temperatureat reflux for 4 h
temperatureUpon cooling to room temperature
customthe mixture was quenched with MeOH (50 mL)
customto remove excess borane
customThe solvent was then evaporated

Sources & evidence

ORD record: ord-82d024e6b77d4fd39487b923d3d2be0c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321731B2

Reaction notes

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