Phenethylamine → 4-bromo-N-phenylbenzamide

HRID 897560Notes

Reaction equation

HRID 897560 reaction equation
C(N)C[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1.C([N:22](CC)CC)C>ClCCl>[C:3]1([NH:22][C:17](=[O:18])[C:14]2[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 6909664-bromo-N-phenylbenzamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenethylamine (1.2 mL, 9.57 mmol) was added slowly to a mixture of 4-Bromo-1-benzenecarbonyl chloride (2.0 g, 9.11 mmol) and triethyl amine (1.9 mL, 13.67 mmol) in dichloromethane (95 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-phenyl-4-bromobenzamide (1.925 g, 69%). 1H NMR (DMSO-d6) δ 2.84 (m, 2H), 3.47 (m, 2H), 7.28 (m, 5H), 7.67 (d, J=8.59 Hz, 2H), 7.76 (d, J=8.59 Hz, 4H), 8.64 (m, 1H).

Workup

  1. customsolvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was re-crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-140c9dc7dea54416b938b222ee096329
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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