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

HRID 221270Notes

Reaction equation

HRID 221270 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([O:19][CH3:20])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>[Cl-].[Na+].O>[Br:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22292805N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 103799108-Bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 1,117.7%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.013 g, 0.03 mmol) methanol (0.5 mL) was treated with 15% aqueous NaOH (0.5 mL), and stirred overnight at 20 C. The product mixture was diluted with brine (5 mL), extracted twice with EtOAc (5 mL), dried with MgSO4, and concentrated to give 0.10 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.08 (s, 1 H), 6.64 (s, 1 H), 3.72 (s, 3 H), 3.2-3.10 (m, 3 H), 2.7-2.5 (m, 3 H), 2.3-2.1 (m, 2 H), 0.96 (d, 3 H), 0.63 (d, 3 H). MS calculated for C14H20BrNO+H: 298, observed: 298.

Workup

  1. extractionextracted twice with EtOAc (5 mL)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e7a277fc95e141ec87cd52812e81ba9e
Source dataset
uspto-grants-2012_06
Patent number
US08207158B2

Reaction notes

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