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

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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.

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