Hydrochloric Acid → 8-Bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

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Reaction Steps

A solution of N-trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.018 g, 0.047 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred for 3 hours at 50 C. The product mixture was brought to pH 7-8 with 10% aqueous HCl, extracted three times with EtOAc (50 mL), dried with MgSO4, and concentrated to give 0.013 g of a white solid. 1H NMR (400 MHz, CD3OD) d 7.10 (s, 1 H), 6.60 (s, 1 H), 3.30 (m, 1H), 3.2−3.0 (m, 2 H), 2.78 (m, 1H), 2.7−2.5 (m, 2H), 2.3−2.1 (m, 2 H), 1.05 (d, 3 H), 0.73 (d, 3 H). MS calculated for C13H18BrNO+H: 284, observed: 284.

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