Hydrochloric Acid → N-Ethyl-4-fluorobenzylamine

HRID 898922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898922
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][C:8](=O)[CH3:9])=[CH:4][CH:3]=1.B.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][CH2:8][CH3:9])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 3532104N-(4-Fluorobenzyl)acetamide

Produkt 1

HCID 4716481N-Ethyl-4-fluorobenzylamineAusbeute 25,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(4-Fluorobenzyl)acetamide (1.344 g, 8.039 mmol) was dissolved in THF (100 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methene compound with borane (1:1) (1.527 g, 20.098 mmol) was added and the mixture was refluxed overnight at RT. HCl (15 ml, 10%) was gently added and was stirred overnight. The solvent was removed by evaporation. Diethyl ether (20 ml) was added and the product was extracted to the water phase by K2CO3 (3×15 ml). The water phase was acidified by HCl (10 ml, 10%) and the product was extracted to the organic phase by EtOAc (3×15 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.309 g of N-(4-fluorobenzyl)ethanamine (yield 25.1%).

Aufarbeitung

  1. temperaturewas cooled to zero degrees under argon atmosphere
  2. customThe solvent was removed by evaporation
  3. additionDiethyl ether (20 ml) was added
  4. extractionthe product was extracted to the water phase by K2CO3 (3×15 ml)
  5. extractionthe product was extracted to the organic phase by EtOAc (3×15 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-53e5602107754c2e8405dd1be097fb73
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351858B2

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