Triethylamine → N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine

HRID 1037646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037646
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[F:10][CH:11]([F:14])[CH2:12][NH2:13].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:13][CH2:12][CH:11]([F:14])[F:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1362742,2-DifluoroethanamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Produkt 1

HCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

41.57 g (256.6 mmol) of 2-chloro-5-chloromethylpyridine, 20.80 g (256.6 mmol) of 2,2-difluoroethane-1-amine and 35.8 ml (256.6 mmol) of triethylamine in 500 ml of acetonitrile are stirred at 45° C. for 21 hours. The reaction mixture is concentrated under reduced pressure and the residue is then taken up in 1 N aqueous hydrochloric acid and the mixture is washed with ethyl acetate. The aqueous phase is made alkaline using 2.5 N aqueous sodium hydroxide solution and extracted repeatedly with ethyl acetate. Concentration of the organic phase under reduced pressure gives 28.6 g (53% of theory) of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethane-1-amine.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. washthe mixture is washed with ethyl acetate
  3. extractionextracted repeatedly with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4f8a9215723646308ee547e9abff6ba2
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546577B2

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