2,5-Difluoronitrobenzene → 1-Benzyl-4-(4-fluoro-2-nitrophenylamino)-piperidine

HRID 2240276

Reaktionsgleichung

Reaktionsgleichung von HRID 2240276
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1CCCCC1=O>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 677672,5-DifluoronitrobenzeneHCID 4158521-Benzyl-4-piperidylamine

Produkt 1

HCID 212627651-Benzyl-4-(4-fluoro-2-nitrophenylamino)-piperidineAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13603N-Methyl-2-piperidoneLösungsmittel

Versuchsvorschrift

2,5-Difluoro-nitrobenzene (21.5 g), 1-benzyl-4-amino-piperidine (52.3 g) and N-methyl-piperidone (100 ml) were stirred at 100° C. for 3 h. After cooling the mixture was partitioned between water and ethyl acetate and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were extracted 5 times with water, and the solvent was evaporated in vacuo. The target compound was crystallized from methanol to yield 38.7 g of the title compound as orange crystals (mp. 86-87° C.).

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. customwas partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. extractionThe combined organic layers were extracted 5 times with water
  5. customthe solvent was evaporated in vacuo
  6. customThe target compound was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-fbc85c14669d45c2a00413062a2b87bd
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723360B2

Verknüpfte Notizen

Wird geladen…