3-Fluorobenzylamine → HCID 178471673, Verbindung

HRID 1257116

Reaktionsgleichung

Reaktionsgleichung von HRID 1257116
C[O-].[Na+].[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8]#[N:9])[CH3:5].[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18]>CO>[CH2:4]([O:6][CH:7]([O:10][CH2:11][CH3:12])[C:8](=[NH:9])[NH:18][CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([F:13])[CH:15]=1)[CH3:5]

Komponenten

5

Edukt 3

HCID 668533-FluorobenzylamineHCID 80223Acetonitrile, 2,2-diethoxy-HCID 10942334Sodium Methoxide

Produkt 1

HCID 178471673HCID 178471673, VerbindungAusbeute 108,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of sodium methoxide (23%, 4.1 mL, 16 mmol) in MeOH was added to a solution of diethoxyacetonitrile (22 g, 86 mmol) in MeOH (400 mL) with stirring. The solution was stirred at room temperature overnight. The solvent was distilled off under reduced pressure. The residue was dissolved in diethyl ethyl (200 mL) and washed with washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was dissolved in MeOH (100 mL), and m-fluorobenzylamine (10 g, 80 mmol) was added. Then this solution was heated under reflux overnight. After cooled to room temperature, the solvent was distilled off under reduced pressure to give the crude title compound (22 g).

Aufarbeitung

  1. stirringThe solution was stirred at room temperature overnight
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ethyl (200 mL)
  4. washwashed
  5. washwith washed with brine (200 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. dissolutionThe crude material was dissolved in MeOH (100 mL)
  10. temperatureThen this solution was heated
  11. temperatureunder reflux overnight
  12. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-851407743c9b4d0c9eac4f36f62a457b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461339B2

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