Potassium Carbonate → 2-(4-Benzyl-1-(5-methoxy-2-nitrophenyl)piperazin-2-yl)acetic acid

HRID 1035274

Reaktionsgleichung

Reaktionsgleichung von HRID 1035274
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][C:15]([O:17]C)=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[N+:28]([O-:30])=[O:29])[CH:10]([CH2:14][C:15]([OH:17])=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 5656543-Fluoro-4-nitroanisoleHCID 156654662-Piperazineacetic acid, 4-(phenylmethyl)-, methyl ester

Produkt 1

HCID 667698072-(4-Benzyl-1-(5-methoxy-2-nitrophenyl)piperazin-2-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of Example 12C (0.907 g, 3.65 mmol) in acetonitrile (11.69 mL) was added 2-fluoro-4-methoxy-1-nitrobenzene (0.50 g, 2.92 mmol) and potassium carbonate (2.019 g, 14.61 mmol) in water (2.92 mL) followed by 18-crown-6 (0.039 g, 0.146 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 24 hours. The solvent was evaporated and water was added followed by dichloromethane. The water phase was washed three times with dichloromethane to remove starting material and then acidified with 1 N HCl until pH=1. The acid product was extracted three times with dichloromethane, dried quickly with sodium sulfate and concentrated to give the title compound. MS (ESI) m/z 386.1 (M+H)+.

Aufarbeitung

  1. temperature(reflux) for 24 hours
  2. customThe solvent was evaporated
  3. additionwater was added
  4. washThe water phase was washed three times with dichloromethane
  5. customto remove
  6. extractionThe acid product was extracted three times with dichloromethane
  7. dry with materialdried quickly with sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b1c81f68774a4c8abfd5117526424148
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546377B2

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