Acetic Acid → 7,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 648956Notes

Reaction equation

HRID 648956 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[C:18]([O:19][CH3:20])=[CH:17][C:10]2[CH2:11][C:12](=O)[NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.[Na]>O1CCOCC1>[CH3:5][O:6][C:7]1[C:18]([O:19][CH3:20])=[CH:17][C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 114017697,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

Product 1

HCID 129234297,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of glacial acetic acid (1.8 g) in dioxan (10 ml) is added dropwise to a suspension of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one (1.3 g, 6 mmol) and sodium borohydridel (1 g, 3 mmol) in dioxan (20 ml), refluxed for 3 hours, concentrated by evaporation and decomposed with water. The mixture is extracted twice with methylene chloride, the extract is concentrated by evaporation and the residue is taken up in ether. After filtration the ether is eliminated in vacuo.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationconcentrated by evaporation
  3. extractionThe mixture is extracted twice with methylene chloride
  4. concentrationthe extract is concentrated by evaporation
  5. filtrationAfter filtration the ether

Sources & evidence

ORD record
ord-527da69bb7b24d09b12664934833b09f
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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