O-Methyltyramine → 4-bromo-N-[2-(3-methoxyphenyl)ethyl]benzamide

HRID 342212Notes

Reaction equation

HRID 342212 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.[C:31](=O)([O-])[OH:32].[Na+]>C(Cl)Cl>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][CH:3]=[C:8]([O:32][CH3:31])[CH:7]=2)=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 4657O-MethyltyramineHCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 110241034-bromo-N-[2-(3-methoxyphenyl)ethyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

29.2 ml of 2-(4-methoxyphenyl)-ethylamine and 34.2 ml of diisopropylethylamine are added dropwise in succession at 0° C. to a solution of 43.9 g of 4-bromobenzoyl chloride in 500 ml of methylene chloride. The reaction mixture is left to warm to room temperature and stirred, subsequently diluted with methylene chloride and treated with saturated sodium hydrogen carbonate solution. The organic phase is washed with saturated sodium hydrogen carbonate solution and then saturated sodium chloride solution, dried and concentrated. There are obtained 66.1 g of 4-bromo-N-[2-(3-methoxy-phenyl)-ethyl]-benzamide, MS: m/e 333 (M+, 1 Br).

Workup

  1. waitThe reaction mixture is left
  2. washThe organic phase is washed with saturated sodium hydrogen carbonate solution
  3. dry with materialsaturated sodium chloride solution, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-968f8083c6c04f11a6de32f11a6d5441
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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