Benzenamine, 3-bromo-4-methyl- → (3-Bromo-4-methyl-phenyl)-[1-(4-chloro-3-methyl-phenyl)-propyl]-amine

HRID 1629704Notes

Reaction equation

HRID 1629704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH3:10])=[CH:4][C:3]=1[CH3:12].[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[CH3:21])[NH2:17].[B][B][B][B][B][B][B][B][B][B]>CO>[Br:13][C:14]1[CH:15]=[C:16]([NH:17][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:12])[CH:4]=2)[CH2:9][CH3:10])[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 82187Benzenamine, 3-bromo-4-methyl-HCID 391041011-(4-Chloro-3-methylphenyl)propan-1-oneHCID 178419135HCID 178419135, compound2×

Product 1

HCID 67343963(3-Bromo-4-methyl-phenyl)-[1-(4-chloro-3-methyl-phenyl)-propyl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of INT 5 (3.00 g, 16.4 mmol) and 3-bromo-4-methylaniline (3.06 g, 16.4 mmol) in MeOH (164 mL) was added decaborane (1.00 g, 8.2 mmol). The reaction mixture was stirred at room temperature overnight. More decaborane (0.50 g, 4.1 mmol) was added. The mixture was stirred at 60° C. for 2 hours. The mixture was concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 8.

Workup

  1. stirringThe mixture was stirred at 60° C. for 2 hours
  2. concentrationThe mixture was concentrated
  3. customThe residue was purified by chromatography on silica gel (heptane/EtOAc)
  4. customto afford INT 8

Sources & evidence

ORD record
ord-ed2fbaee727e43b5aeaa740330c55434
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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