N-bromobutanimide → HCID 22292777, compound

HRID 1035331Notes

Reaction equation

HRID 1035331 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:21]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:21])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22292800HCID 22292800, compound

Product 1

HCID 22292777HCID 22292777, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.25 g, 4.35 mmol) in acetonitrile (40 mL) was treated with N-bromosuccinimide (0.852 g, 4.79 mmol) and stirred overnight at 20 C. The product mixture was diluted with EtOAc (200 mL), washed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 1.55 g of a clear oil. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.34 (s, 1 H), 6.65 (m, 1 H), 3.87 (s, 3 H), 3.81 (m, 1 H), 3.55 (m, 1.3 H), 3.37 (m, 0.7 H), 3.2-2.9 (bm, 4 H), 1.30 (m, 3 H). MS calculated for C14H15BrF3NO2+H: 366, observed: 366.

Workup

  1. washwashed with saturated aqueous sodium bisulfite (100 mL) and brine (100 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0b238ef5481f4015bff753cafa351ca1
Source dataset
uspto-grants-2013_10
Patent number
US08546379B2

Reaction notes

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