N-bromobutanimide → N-trifluoroacetyl-8-bromo-1-ethyl-7-methoxy-2,3,4,5tetrahydro-1H-3-benzazepine

HRID 1035357Notes

Reaction equation

HRID 1035357 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH2:12][CH3:13])[C:9]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:22]N1C(=O)CCC1=O>C(#N)C>[F:21][C:2]([F:1])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH2:12][CH3:13])[C:9]2[CH:14]=[C:15]([Br:22])[C:16]([O:18][CH3:19])=[CH:17][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22292778HCID 22292778, compound

Product 1

HCID 22292824N-trifluoroacetyl-8-bromo-1-ethyl-7-methoxy-2,3,4,5tetrahydro-1H-3-benzazepineYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-trifluoroacetyl-1-ethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.710 g, 2.36 mmol) in acetonitrile (20 mL) was treated with N-bromosuccinimide (0.504 g, 2.83 mmol), and stirred overnight at 20 C. The product mixture was concentrated, diluted with EtOAc (100 mL), washed with water (50 mL) and brine (50 mL), dried with Na2SO4 and concentrated. Flash chromatography (10% EtOAc in hexanes, silica) resulted in 0.561 g of a clear oil. MS calculated for C15H17BrF3NO2+H: 380, observed: 380.

Workup

  1. concentrationThe product mixture was concentrated
  2. additiondiluted with EtOAc (100 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97f6297217804b27883514fcfa96c3cb
Source dataset
uspto-grants-2013_10
Patent number
US08546379B2

Reaction notes

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