Sodium Hydroxide → 8-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1035126Notes

Reaction equation

HRID 1035126 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Br:21][C:14]1[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292803N-Trifluoroacetyl-8-bromo-7-isopropoxy-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 100175568-Bromo-7-isopropoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 76.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

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) δ 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.

Workup

  1. extractionextracted twice with EtOAc (5 mL)
  2. washthe combined organic phases were washed with brine (3 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f25fc9500dce4b0eaf3096cb1388bb63
Source dataset
uspto-grants-2013_10
Patent number
US08546378B2

Reaction notes

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