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

HRID 84101Notes

Reaction equation

HRID 84101 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH2:12][CH3:13])[C:9]2[CH:14]=[C:15]([Br:20])[C:16]([O:18][CH3:19])=[CH:17][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.[Cl-].[Na+].O>[Br:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH2:12][CH3:13])[C:9]=2[CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292824N-trifluoroacetyl-8-bromo-1-ethyl-7-methoxy-2,3,4,5tetrahydro-1H-3-benzazepine

Product 1

HCID 99940088-Bromo-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.561 g, 1.48 mmol) in methanol (30 mL) was treated with 15% aqueous NaOH (30 mL), and stirred overnight at 20 C. The product mixture was diluted with brine (100 mL), extracted twice with EtOAc (200 mL), dried with MgSO4, and concentrated to give 0.412 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.24 (s, 1H), 6.76 (s, 1H), 3.83 (s, 3H), 3.02 (m, 3H), 2.91 (s, 1H), 2.85-2.76 (m, 3H), 2.63 (m, 1H), 1.78 (m, 1H), 1.72 (m, 1H), 0.94 (dd, J=8, 8 Hz, 3H). MS calculated for C13H18BrNO+H: 284, observed: 284.

Workup

  1. extractionextracted twice with EtOAc (200 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e9ba40bbd1c9437aa078a582d36bfd6b
Source dataset
uspto-grants-2014_09
Patent number
US08846906B2

Reaction notes

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