Phenethylamine → 2-bromo-3-methyl-N-phenethylbenzamide

HRID 1028941Notes

Reaction equation

HRID 1028941 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3][CH:2]=1.[Br:10][C:11]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>C(Cl)Cl.O>[Br:10][C:11]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:14]

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 141743752-Bromo-3-methylbenzoyl chloride

Product 1

HCID 712532462-bromo-3-methyl-N-phenethylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenethylamine (0.28 mL, 2.195 mmol) in DCM (2.0 mL) was added 2-bromo-3-methylbenzoyl chloride (0.15 mL, 0.998 mmol) dropwise via syringe at ambient temperature. Mixture was allowed to stir overnight, then diluted with water (30 mL) and extracted with DCM (30 mL). The organic extract was washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give 2-bromo-3-methyl-N-phenethylbenzamide as a white solid.

Workup

  1. extractionextracted with DCM (30 mL)
  2. extractionThe organic extract
  3. washwas washed with 1N HCl (2×25 mL) and 1N NaOH (2×25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09fae2f94c0541a9ac82423fe7e4d621
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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