Piperidine → 2-Nitro-5-piperidinoaniline

HRID 272699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272699
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:8][C:6]=1[NH2:7])([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Produkt 1

HCID 70622462-Nitro-5-piperidinoanilineAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-chloro-2-nitroaniline (1.73 g, 10 mmol), piperidine (1.09 mL, 11 mmol), and K2CO3 (1.52 g, 11 mmol) in DMF was heated to 120° C. for 24 hours. Cooled to room temperature. Partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide 1.33 g (60%) of the desired product. MS (ESI) m/e 222 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 7.79 (d, J=9.83 Hz, 1H), 7.22 (s, 2H), 6.37 (dd, J=9.83, 2.71 Hz, 1H), 6.19 (d, J=2.71 Hz, 1H), 3.34-3.38 (m, 4H), 1.53-1.60 (m, 6H).

Aufarbeitung

  1. temperatureCooled to room temperature
  2. customPartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-65017cb31ba246ceaa4893c401fc9ae0
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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