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

HRID 2290212Notes

Reaction equation

HRID 2290212 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.[BH4-].[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 4311764Sodium borohydrideHCID 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 1.8 gm of glacial acetic acid in 10 ml of dioxane is added dropwise to a suspension of 1.3 gm (6 mmol) of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 1.1 gm (3 mmol) of sodium borohydride in 20 ml of dioxane, and the resulting mixture is refluxed for three hours, concentrated by evaporation, and mixed 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 removed in vacuo.

Workup

  1. temperaturethe resulting mixture is refluxed for three hours
  2. concentrationconcentrated by evaporation
  3. additionmixed with water
  4. extractionThe mixture is extracted twice with methylene chloride
  5. concentrationthe extract is concentrated by evaporation
  6. filtrationAfter filtration
  7. customthe ether is removed in vacuo

Sources & evidence

ORD record
ord-906a7206d94f4e72adffe58125785846
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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