Ethylenediamine → HCID 2990663, Verbindung

HRID 911294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911294
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1.[Cu](C#N)[C:19]#[N:20].C(N)CN>CN(C=O)C>[C:19]([C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1)#[N:20]

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 90711954-Bromo-N-cyclohexyl-2-fluorobenzamideHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 2990663HCID 2990663, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Heat a mixture of 4-bromo-N-cyclohexyl-2-fluoro-benzamide (1.24 g, 4.13 mmol) and copper cyanide (740 mg, 8.26 mmol) in DMF (20 mL) to reflux for 16 h. Cool the mixture to ambient temperature, add aqueous ethylenediamine and stir for 30 min. Extract the mixture with hexane/EtOAc (1:1), dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1) to give the desired intermediate as a white solid (620 mg, 61%). MS (ES−) m/z: 245 (M−H)−.

Aufarbeitung

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. extractionExtract the mixture with hexane/EtOAc (1:1)
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-e1850e6bbbc04e72b25e917297cdd054
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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