Borane;tetrahydrofuran → N-benzyl-N'-(4-fluoro-2-methyl-phenyl)-ethane-1,2-diamine

HRID 2065754

Reaktionsgleichung

Reaktionsgleichung von HRID 2065754
[CH2:1]([NH:8][C:9](=O)[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.B>C1COCC1>[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 17954343N-Benzyl-2-(4-fluoro-2-methyl-phenylamino)acetamide

Produkt 1

HCID 68751810N-benzyl-N'-(4-fluoro-2-methyl-phenyl)-ethane-1,2-diamineAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-benzyl-2-(4-fluoro-2-methyl-phenylamino)-acetamide (17 g) in THF (500 mL) was added a solution of borane tetrahydrofuran complex (499.4 mL, 1M in THF). The solution was heated to reflux for 4 h, was concentrated and redissolved in a mixture of 2M HCl and TBME. The inorganic phase was extracted with TBME, the organic phases washed with 2M HCl. The pH of the combined inorganic phases was adjusted to pH 11 by the addition of concentrated NaOH, and the solution was extracted with TBME. The combined organic phases were dried (Na2SO4), filtered and evaporated to yield N-benzyl-N′-(4-fluoro-2-methyl-phenyl)-ethane-1,2-diamine (15.1 g) as a crude product, MS: 259.3 ([M+H]+).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 4 h
  3. concentrationwas concentrated
  4. dissolutionredissolved in a mixture of 2M HCl and TBME
  5. extractionThe inorganic phase was extracted with TBME
  6. washthe organic phases washed with 2M HCl
  7. additionThe pH of the combined inorganic phases was adjusted to pH 11 by the addition of concentrated NaOH
  8. extractionthe solution was extracted with TBME
  9. dry with materialThe combined organic phases were dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ec1d4bbfe95b45ec9185cd3fc3c1cce3
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288541B2

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