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

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Reaction Steps

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.

Provenance & Evidence