Water → 7-Methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine

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Reaction Steps

To a solution of 7-methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo-[d]azepine (6.62 g, 20 mmol) in anhydrous THF (150 ml) is added a solution of LiAlH4 in THF (1.0 M, 40 ml, 2.0 eq.). The resulting mixture is refluxed under N2 for 24 hr. To the solution at 0° C. is added water (1.52 g) very carefully with stirring, followed by the addition of sodium hydroxide solution (10.0 N, 1.52 ml) and then water (3.04 g). The mixture is stirred at rt for an additional 1 hr, then diluted with EtOAc (300 ml), and dried with magnesium sulfate (40.0 g). After filtration, and washing the filtering cake with EtOAc (100 ml×3), the combined organic phase is evaporated to dryness under reduced pressure to give the title compound. MS (+VE) m/z 178.1 (M++1).

Provenance & Evidence