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

HRID 1035358Notes

Reaction equation

HRID 1035358 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, 1 H), 6.76 (s, 1 H), 3.83 (s, 3 H), 3.02 (m, 3 H), 2.91 (s, 1 H), 2.85-2.76 (m, 3 H), 2.63 (m, 1 H), 1.78 (m, 1 H), 1.72 (m, 1 H), 0.94 (dd, J=8, 8 Hz, 3 H). 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-b8300029fcf64d129226619d63a84477
Source dataset
uspto-grants-2013_10
Patent number
US08546379B2

Reaction notes

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