Potassium Carbonate → 4-(4-Methylpiperazin-1-yl)benzaldehyde

HRID 396872

Reaktionsgleichung

Reaktionsgleichung von HRID 396872
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.F[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>O>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 680234-Fluorobenzaldehyde

Produkt 1

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
101.5 °C

Versuchsvorschrift

Potassium carbonate (3.3 g, 24 mmol) and 1-methylpiperazine (2.8 g, 29 mmol) were dissolved in 16 mL of water and then 4-fluorobenzaldehyde (2.0 g, 16 mmol) was added. The mixture was heated at reflux (100-103° C.) under a nitrogen atmosphere for 21 hours when HPLC showed that the reaction was complete. The solution was cooled to 20-25° C. and then extracted with methylene chloride (2×30 mL). The methylene chloride extracts were combined, washed with water (2×30 mL), and then concentrated at reduced pressure to a yellow oil (3.1 g, 96% yield). The crude solid was triturated with hexanes to afford crystals. mp 60.5-62.0° C. 1H NMR (CDCl3) δ 9.77 (s, 1H), 7.74 (d, J=10 Hz, 2H), 6.91 (d, J=10 Hz, 2H), 3.40 (m, 4H), 2.53 (m, 4H), and 2.34 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureThe solution was cooled to 20-25° C.
  3. extractionextracted with methylene chloride (2×30 mL)
  4. washwashed with water (2×30 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b6cc50fd33914429bf6722e26ec59920
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608195B2

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