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

HRID 432264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432264
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 22346935N1-phenethyl-4-bromo-2-methoxybenzamideAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d07c2f44ff5d4c94920b1f54caec2816
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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