Maleic Acid → (4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone Bis-maleate Salt

HRID 13548

Reaktionsgleichung

Reaktionsgleichung von HRID 13548
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29]>CCO.CCOCC>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:16][CH:17]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 444266Maleic AcidHCID 10042344(4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone

Produkt 1

HCID 86612816(4-Isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl-phenyl)-methanone Bis-maleate Salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of (4-isopropyl-piperazin-1-yl)-(4-morpholin-4-ylmethyl -phenyl)-methanone (34.0 g, 102.7 mmol) in absolute EtOH (200 mL) was added, via an addition funnel, a solution of maleic acid (23.9 g, 206 mmol) in absolute EtOH (200 mL) over 15 min. The resulting suspension was stirred at room temperature for 30 min, at 75° C. for 1 h, and was then allowed to cool to room temperature over 16 h. The reaction mixture was cooled further to 0° C. and was stirred for 2 h. The reaction mixture was diluted with Et2O (50 mL) and stirred for 30 min. The resulting precipitate was collected by suction filtration, washed with cold EtOH/Et2O (4:1,100 mL×2), and dried in a vacuum oven at 40° C. for 20 h to yield the title compound as crude material, as a white solid.

Aufarbeitung

  1. temperatureto cool to room temperature over 16 h
  2. temperatureThe reaction mixture was cooled further to 0° C.
  3. stirringwas stirred for 2 h
  4. stirringstirred for 30 min
  5. filtrationThe resulting precipitate was collected by suction filtration
  6. washwashed with cold EtOH/Et2O (4:1,100 mL×2)
  7. customdried in a vacuum oven at 40° C. for 20 h

Quellen und Nachweise

ORD-Eintrag
ord-41b12b4783d5423b86149fc6c44bbae9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728129B2

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