Phenethylamine → N1-phenethyl-4-bromo-2-methoxybenzamide

HRID 897554Notes

Reaction equation

HRID 897554 reaction equation
[CH2:1]([NH2:9])[CH2:2][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])=[C:13]([O:20][CH3:21])[CH:12]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([NH:9][C:17](=[O:18])[C:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]=1[O:20][CH3:21])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 223467824-Bromo-2-methoxybenzoyl chloride

Product 1

HCID 22346935N1-phenethyl-4-bromo-2-methoxybenzamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenethylamine (0.79 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 2 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 purified by flash column chromatography using dichloromethane/ethyl acetate (97:3) as mobile to give N1-phenethyl-4-bromo-2-methoxybenzamide (1.81 g, 90%). 1H NMR (DMSO-d6) δ 2.83 (m, 2H), 3.50 (m, 2H), 3.84 (s, 3H), 7.31 (m, 7H), 7.65 (d, J=8.28 Hz, 1H), 8.15 (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 purified by flash column chromatography

Sources & evidence

ORD record
ord-a4ca78be4255462dacd821c99046e444
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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