Benzylethanolamine → N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

HRID 595798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595798
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:11])[CH:3]=1.CCN(C(C)C)C(C)C.[CH2:21]([NH:28][CH2:29][CH2:30][OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([N:28]([CH2:29][CH2:30][OH:31])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[F:11])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 4348BenzylethanolamineHCID 81531DiisopropylethylamineHCID 27340264-Bromo-2-fluorobenzoyl chloride

Produkt 1

HCID 60740299N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-2-fluorobenzoyl chloride (1 g, 4.21 mmol) in THF (14.04 mL) was added DIEA (1.103 mL, 6.32 mmol) and 2-(benzylamino)ethanol (0.764 g, 5.05 mmol) at room temperature. The reaction mixture was stirred for overnight. The reaction mixture was extracted with EtOAc. The organic layer was washed with water and brine. After dried over anhydrous sodium sulfate, filtered and concentrated in vacuo, the crude N-benzyl-4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide was used for the next step (83%). LCMS (m/z): 352/354 (MH+), 0.83 min.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialAfter dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custom352/354 (MH+), 0.83 min.

Quellen und Nachweise

ORD-Eintrag
ord-4c5111933f814b6b9d1e4a3acd4384d0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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