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

HRID 84084Notes

Reaction equation

HRID 84084 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:20])[C:15]([O:17][CH2:18][CH3:19])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[Br:20][C:14]1[C:15]([O:17][CH2:18][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 22292768N-Trifluoroacetyl-8-bromo-7-ethoxy-1-methyl-2,3, 4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 104016028-Bromo-7-ethoxy-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 94.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-ethoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.010 g, 0.026 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 0.007 g of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.29 (s, 1H), 6.63 (s, 1H), 4.07 (q, J=6 Hz, 2H), 3.03 (m, 3H), 2.91 (m, 3H), 2.73 (m, 1H), 2.26 (bs, 1H), 1.46 (t, J=6 Hz, 3H), 1.32 (d, J=7 Hz, 3H). MS calculated for C15H17BrF3NO2+H: 380, observed: 380.

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-5ae3e1d19d344d3ca60c6aadc895bffb
Source dataset
uspto-grants-2014_09
Patent number
US08846906B2

Reaction notes

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