Sodium Hydroxide → 7-Allyloxy8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 881950Notes

Reaction equation

HRID 881950 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:23])[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.[Cl-].[Na+].O>[CH2:20]([O:19][C:17]1[C:16]([Br:23])=[CH:15][C:9]2[CH:10]([CH:12]([CH3:13])[CH3:14])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:18]=1)[CH:21]=[CH2:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22292818N-Trifluoroacetyl-7-allyloxy-8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 100191247-Allyloxy8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 118.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-trifluoroacetyl-7-allyloxy-8-bromo-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.011 g, 0.026 mmol) in methanol (0.5 mL) was treated with of 15% aqueous NaOH (0.5 mL), and stirred for 3 hours at 50 C. The product mixture was diluted with brine (5 mL), extracted twice with EtOAc (5 mL), dried with MgSO4, and concentrated to give 0.010 g of a clear oil. 1H NMR (400 MHz, CD3OD) d 7.09 (s, 1H), 6.62 (s, 1H), 5.94 (m, 1H), 5.32 (dd, 1H), 5.12 (dd, 1H), 4.46 (d, 2H), 3.19 (m, 1H), 3.05 (m, 2H), 2.66 (m, 1H), 2.5 (bm, 2H), 2.3-2.1 (m, 2H), 0.95 (d, 3H), 0.63 (d, 3H). MS calculated for C16H22BrNO+H: 324, observed: 324.

Workup

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

Sources & evidence

ORD record
ord-bdf418047ed64136947c7783ae590970
Source dataset
uspto-grants-2015_03
Patent number
US08993750B2

Reaction notes

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