Sodium Hydroxide → 5,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 888095Notes

Reaction equation

HRID 888095 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=O)[NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 570064745,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.5 g, 8.0 mmol) was dissolved into THF (20 ml) and cooled down to 0° C. LAH (0.5 g 60% in oil, 13 mmol) was added in portions. The reaction was heated to reflux for 2 h. TLC showed a new spot alongside staring lactam. Another 360 mg of LAH was added and the mixture was heated for 2 h. H2O was added until sizzling stopped followed by 2N NaOH. Stirred for 15 min at RT. Na2SO4 (3.8 g) was added and the mixture was stirred for 15 min followed by filtration over Celite®. Diluted with EtOAc and washed with H2O, dried (MgSO4), filtered and concentrated to give 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. temperaturethe mixture was heated for 2 h
  4. stirringthe mixture was stirred for 15 min
  5. filtrationfollowed by filtration over Celite®
  6. additionDiluted with EtOAc
  7. washwashed with H2O
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9d0d82ddc0e04ca0a25d7e7b44c8bde8
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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