Potassium Carbonate → HCID 23117202, Verbindung

HRID 716364

Reaktionsgleichung

Reaktionsgleichung von HRID 716364
C(=O)([O-])[O-].[K+].[K+].[N:7]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[F:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:30]=1F)[C:24]([O:26][CH3:27])=[O:25]>>[F:20][C:21]1[CH:22]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[CH:28]=[CH:29][C:30]=1[N:10]1[CH2:11][CH2:12][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:9]1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2775358Methyl 3,4-difluorobenzoate

Produkt 1

HCID 23117202HCID 23117202, VerbindungAusbeute 44,9 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Potassium carbonate (5.56 g, 40.3 mmol) and tert-butyl piperazine-1-carboxylate (6.92 g, 37.2 mmol) were combined, methyl 3,4-difluorobenzoate (5.33 g, 31.0 mmol) was added and the reaction mixture was stirred at 90° C. for 1 d. The mixture was triturated with ethyl acetate (3×5 mL) and the combined organic extracts were filtered. This was concentrated down to about 5-10 mL and subjected to flash column chromatography on silica gel (120 g SiO2, hexanes:ethyl acetate 1:0 to 4:1) to afford tert-butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (4.702 g, 13.90 mmol, 44.9% yield) as a white solid. ESI-MS: m/z 339 (M+H)+.

Aufarbeitung

  1. customThe mixture was triturated with ethyl acetate (3×5 mL)
  2. filtrationthe combined organic extracts were filtered
  3. concentrationThis was concentrated down to about 5-10 mL

Quellen und Nachweise

ORD-Eintrag
ord-2ae977c34a62416e8e8c52bb6288cbc1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187497B2

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