Reaction #171268

Reaction equation

N-trifluoroacetyl-8-bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

NaOH

→

clear oil

Yield 76.6%

8-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Yield 76.6%

Solvents

water

methanol

Conditions

Workup

1. 1
   Extractionextracted twice with EtOAc (5 mL)
2. 2
   Washthe combined organic phases were washed with brine (3 mL)
3. 3
   Dryingdried with Na2SO4
4. 4
   Concentrationconcentrated

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.014 g, 0.035 mmol) in methanol (1 mL) was treated with 15% aqueous NaOH (1 mL), and stirred overnight at 20 C. The product mixture was diluted with water (3 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (3 mL), dried with Na2SO4 and concentrated to give 0.008 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.24 (s, 1H), 6.64 (s, 1H), 4.48 (m, 1H), 2.98 (m, 3H), 2.87 (m, 3H), 1.36 (m, 6H), 1.30 (d, J=7 Hz, 3H). MS calculated for C14H20BrNO+H: 298, observed: 298.

Source