Potassium Carbonate → Ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoate

HRID 1633602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633602
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:24]=[C:25]([NH:26][C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=3[N+:13]([O-:15])=[O:14])[CH:27]=[CH:28][CH:29]=2)[CH2:18]1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 1268247Ethyl 4-chloro-3-nitrobenzoateHCID 22741929HCID 22741929, Verbindung

Produkt 1

HCID 22741906Ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoateAusbeute 98 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1c (5.7 g, 25 mmol), 2j (3.8 g, 20 mmol) and potassium carbonate (3.45 g, 25 mmol) was heated to 70° C. under a stream of nitrogen. The resulting melt was stirred at 70° C. overnight. The reaction mixture was partitioned between water and ethyl acetate and the organic phase was extracted with diluted hydrochloric acid (4M). The aqueous phase was rendered alkaline by addition of aqueous sodium hydroxide (4M) and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure to leave ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoate (7.5 g, 98%) as an oil.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionthe organic phase was extracted with diluted hydrochloric acid (4M)
  3. additionby addition of aqueous sodium hydroxide (4M)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d53fe524b96b48ebb269cb5f7d58a262
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503925B1

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