Dimethylformamide → Mofegiline

HRID 1489918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489918
C([N-:3][CH:4]=O)=O.[Na+].C(#N)C.CN(C)C=O.ClC/[C:17](=[CH:27]/[F:28])/[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1>O>[NH2:3][CH2:4]/[C:17](=[CH:27]/[F:28])/[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 9815806(E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butaneHCID 10877056Sodium Diformylamide

Produkt 1

HCID 6437850Mofegiline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Combine sodium diformylamide (28.8 g, 0.31 mol), acetonitrile (360 g), and N,N-dimethylformamide (48 g). Add (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane (50.6 g, 0.23 mol). Heat to reflux. After 5 hours, cool to ambient temperature. Add water (466 g) and stir for 15 minutes. After 30 minutes, the aqueous layer is removed. Evaporate the organic layer in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ 2.28 (m, 2H), 2.72 (m, 2H), 4.07 (d, J=3Hz, 2H), 6.74 (d, J=81Hz, 1H), 6.94 (m, 2H), 7.13 (m, 2H), 8.73 (s, 2H).

Aufarbeitung

  1. temperatureHeat to reflux
  2. waitAfter 30 minutes
  3. customthe aqueous layer is removed
  4. customEvaporate the organic layer in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f52939ca02f4d06bb71776030f1d679
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05679854

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