[BH4-].[Na+].C([Se][Se]CC1C=CC=CC=1)C1C=CC=CC=1.ClC(Cl)(Cl)C([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1)O.[OH-:38].[Na+].[CH2:40]([OH:42])[CH3:41]>>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([C:26]2[CH:27]=[CH:28][C:23]([CH2:41][C:40]([OH:38])=[O:42])=[CH:24][CH:25]=2)[CH2:30][CH2:31]10.559 g (14.77 mmol) of sodium borohydride is added quickly to 2.294 g (7.35 mmol) of dibenzyl diselenide in 28 ml of ethanol. The reaction mixture is stirred at room temperature for 1 hour. 2.266 g (7 mmol) of 2,2,2-trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanol and 1.680 g (42.0 mmol) of sodium hydroxide are then added. The reaction mixture is stirred at 35° C. for 24 hours. The solvent is concentrated and the crude product extracted with ethyl acetate after adding a pH 5 aqueous phase. The organic phases are combined, dried on magnesium sulfate and then concentrated to yield 2-(4-(4-methylpiperazine-1-yl)phenyl)acetic acid which is used without additional purification.
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