Piperidine → 2-Nitro-3-(piperidin-1-yl)aniline

HRID 334499

Reaktionsgleichung

Reaktionsgleichung von HRID 334499
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[N+:9]([C:3]1[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])([O-:11])=[O:10]

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1010683-Chloro-2-nitroaniline

Produkt 1

HCID 125972682-Nitro-3-(piperidin-1-yl)anilineAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3-chloro-2-nitroaniline (CXXI) (2.00 g, 11.6 mmol, 1 eq) and piperidine (2.95 g, 34.7 mmol, 3 eq) in DMF (60 ml) was added K2CO3 (4.78 g, 34.4 mmol, 3 eq) in one portion and the mixture was stirred at 120° C. under nitrogen overnight. The reaction mixture was diluted with ethyl acetate (60 ml) and washed with saturated NaHCO3 solution (50 mL). The organic phases were dried over Na2SO4 and concentrated in vacuo, the resultant residue was purified by silica gel column chromatography (PE:EtOAc=5:1→1:1) to give 2-nitro-3-(piperidin-1-yl)aniline (CXXII) (1.8 g, 8.14 mmol, 70.3% yield) as a black solid. ESIMS found for C11H15N3O2 m/z 222 (M+H).

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution (50 mL)
  2. dry with materialThe organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe resultant residue was purified by silica gel column chromatography (PE:EtOAc=5:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7f8b2d13be7047229a65ac2000eb1803
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883822B2

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