Hexahydro-1,4-diazepine → 1-[5-(Trifluoromethyl)pyridin-2-yl]-1,4-diazepane

HRID 1923482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923482
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH:12]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 68163Hexahydro-1,4-diazepineHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 27607791-[5-(Trifluoromethyl)pyridin-2-yl]-1,4-diazepane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-trifluoromethylpyridine (362 mg, 1.99 mmol) and [1,4]-diazepane (1000 mg, 9.98 mmol) in DMF (6.0 mL) is stirred for 2 hours at room temperature followed by evaporation of the solvent DMF under vacuo. The residue is distributed between ethyl acetate (30 mL) and water (40 mL). The aqueous phase is extracted once with ethyl acetate (20 m) and the combined organic phases are dried with Na2SO4. Evaporation gives an oily residue (crude 1-(5-trifluoromethyl-pyridin-2-yl)-[1,4]-diazepane) which is used directly for reductive amination in the last step.

Aufarbeitung

  1. customfollowed by evaporation of the solvent DMF under vacuo
  2. extractionThe aqueous phase is extracted once with ethyl acetate (20 m)
  3. dry with materialthe combined organic phases are dried with Na2SO4
  4. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-85ab660f24094748a431a01a41def725
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178526B2

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