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

HRID 1380854Notes

Reaction equation

HRID 1380854 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 glacial acetic acid (1.8 g) in dioxan (10 ml) is added to a suspension of 7,8-dimethoxy-1,3,4,5-tetrahydro-2-H-3-benzazepin-2-one (1.3 g, 6 mmol) and sodium borohydride (1.1 g, 3 mmol) in dioxan (20 ml). The resulting mixture is refluxed for 3 hours, evaporated 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 filtering, the ether is eliminated in vacuo. Yield: 1.1 g. Mp: 86°-89° C.

Workup

  1. temperatureThe resulting mixture is refluxed for 3 hours
  2. customevaporated
  3. additionmixed with water
  4. extractionThe mixture is extracted twice with methylene chloride
  5. concentrationthe extract is concentrated by evaporation
  6. filtrationAfter filtering

Sources & evidence

ORD record
ord-5236a1e9b152418fb3d3c2d5b175336e
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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