Tetrahydrofuran → 1-(4-Formylbenzoyl)-4-isopropylpiperazine

HRID 13536

Reaktionsgleichung

Reaktionsgleichung von HRID 13536
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+].[CH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)=[O:18]>O>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:17]([C:19]2[CH:27]=[CH:26][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)=[O:18])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 780131-Isopropylpiperazine2×HCID 124246204-Formylbenzoyl chloride

Produkt 1

HCID 574785811-(4-Formylbenzoyl)-4-isopropylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

4-Isopropyl-piperazine (79.53 g, 0.620 mol), THF (444 g, 5.04 mol), water (36 g, 2 mol) and a 50% solution of sodium hydroxide (130.6 g, 1.63 mol) were charged to a reaction vessel and cooled to 0-5° C. 4-Formyl-benzoyl chloride in THF (110.08 g, 0.630 mol) was added to the 4-isopropyl-piperazine reaction mixture while maintaining the temperature below about 10° C. The resulting white suspension was stirred at room temperature until the reaction was deemed complete. Water was added to the reaction slurry and the resulting hazy solution was filtered over Celite to remove insolubles. The filtered reaction solution was settled and the water layer was removed. The product/THF layer was dried sequentially with magnesium sulfate and molecular sieves. The product solution (KF≦0.5%) was stored at 5° C. for use without further manipulations.

Aufarbeitung

  1. temperaturewhile maintaining the temperature below about 10° C
  2. filtrationthe resulting hazy solution was filtered over Celite
  3. customto remove insolubles
  4. customThe filtered reaction solution
  5. customthe water layer was removed
  6. dry with materialThe product/THF layer was dried sequentially with magnesium sulfate and molecular sieves
  7. customwas stored at 5° C. for use without further manipulations

Quellen und Nachweise

ORD-Eintrag
ord-aec267aab7a3492ea2e6faaccc86e556
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728129B2

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