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

HRID 1154633Notes

Reaction equation

HRID 1154633 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 was added dropwise to a suspension of 1.3 gm (6 mmols) of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 1.1 gm (3 mmols) of sodium borohydride in 20 ml of dioxane; the mixture was refluxed for 3 hours, concentrated by evaporation and mixed with water. The mixture was extracted twice by shaking with methylene chloride; the extract was concentrated by evaporation, and the residue was taken up in ether. After filtering, the ether was removed in vacuo.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationconcentrated by evaporation
  3. additionmixed with water
  4. extractionThe mixture was extracted twice
  5. concentrationthe extract was concentrated by evaporation
  6. filtrationAfter filtering
  7. customthe ether was removed in vacuo

Sources & evidence

ORD record
ord-2e1d057e184f4534b76a690d0831fb19
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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