Maleic Acid → (4-Isopropyl-piperazin-1-yl)-(4-piperidin-1-ylmethyl-phenyl)-methanone, bis-maleate salt

HRID 560988Notes

Reaction equation

HRID 560988 reaction equation
[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][CH2:22][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:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 10359235(1-Isopropylpiperidin-4-yl)(4-(piperidin-1-ylmethyl)phenyl)methanone

Product 1

HCID 131728158(4-Isopropyl-piperazin-1-yl)-(4-piperidin-1-ylmethyl-phenyl)-methanone, bis-maleate salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a mechanically agitated solution of (4-isopropyl-piperazin-1-yl)-(4-piperidin-1-ylmethyl-phenyl)-methanone (40.0 g, 122 mmol) in absolute EtOH (800 mL) was added, via an addition funnel, a solution of maleic acid (28.2 g, 243 mmol) in absolute EtOH (200 mL) over 30 min. The resulting suspension was stirred at room temperature for 16 h, then diluted with Et2O (200 mL), cooled to 0° C., and stirred for 2 h. The precipitate was collected by suction filtration, washed with cold EtOH/Et2O (4:1, 3×100 mL). The solids were dried under vacuum to yield crude title compound as a white solid.

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for 2 h
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with cold EtOH/Et2O (4:1, 3×100 mL)
  5. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-a599556fa1394627a8e00bb15c5ac4df
Source dataset
uspto-grants-2011_11
Patent number
US08063206B2

Reaction notes

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