[CH2:1]([Mg]Cl)C.[C:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(=[O:7])[CH3:6].C(OCC)C.[Cl-].[NH4+]>C1COCC1>[OH:7][C:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]2)=[CH:12][CH:13]=1)([CH3:1])[CH3:6]
Ethyl magnesium chloride (3M) in anhydrous THF (10 ml) was treated at room temperature under argon with a solution of 1-(4-acetylphenyl)-4-(4-pyridyl)piperazine (281 mg) in anhydrous THF (15 ml). The resulting solid suspension was heated at 70° C. under reflux for 3 hours. The mixture was cooled in ice at 0-5° C. and treated with diethyl ether and a saturated solution of aqueous ammonium chloride. The reaction mixture was stirred for 10 minutes with ice cooling and at room temperature for 10 minutes. The aqueous phase was then extracted with dichloromethane and the ether phase was evaporated. The residue was dissolved in dichloromethane and combined with the other organic extracts. The combined extracts were then washed with saturated brine, dried over MgSO4, filtered and evaporated to give an impure orange solid. The solid was purified by chromatography on a prepacked silica column (“Varian bond elut-trademark), eluting with a mixture of methanol (1-2%) and ammonium hydroxide (1%) in dichloromethane to obtain a pale yellow solid which was triturated with diethyl ether to give 1-(4-(1-hydroxy-1-methylethyl)phenyl)4-(4-pyridyl)piperazine (21% yield) as a pale yellow solid, m.p. 234-235° C.
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