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

HRID 221265Notes

Reaction equation

HRID 221265 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-58d82925c30f4cc6a0979b4b231a5a4f
Source dataset
uspto-grants-2012_06
Patent number
US08207158B2

Reaction notes

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