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

HRID 2108536Notes

Reaction equation

HRID 2108536 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]2[CH2:14][CH2:13]2)[C:9]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Br:23]N1C(=O)CCC1=O>C(#N)C>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]2[CH2:14][CH2:13]2)[C:9]2[CH:15]=[C:16]([Br:23])[C:17]([O:19][CH3:20])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22292780HCID 22292780, compound

Product 1

HCID 22292775N-Trifluoroacetyl-8-bromo-1-cyclopropyl-7-methoxy-2,3,4,5-tetrahydro 1H-3-benzazepineYield 44.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-trifluoroacetyl-1-cyclopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.025 g, 0.08 mmol) in acetonitrile (1 mL) was treated with N-bromosuccinimide (0.032 g, 0.18 mmol) and stirred for 2 hrs. at 50 C. The product mixture was concentrated and then purified by flash chromatography (10% EtOAc in hexanes, silica) resulting in 0.014 g of a white solid. MS calculated for C15H15BrF3NO2+H: 378, observed: 378.

Workup

  1. concentrationThe product mixture was concentrated
  2. custompurified by flash chromatography (10% EtOAc in hexanes, silica)

Sources & evidence

ORD record
ord-6670aca8e55d4487b6db863e7814854c
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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