Br[CH2:2][C:3]1(C)[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.Cl.ClC1C=CC=CC=1N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:2][CH:3]1[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1
A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g), 1-(2-chlorophenyl)piperazine hydrochloride (1.4 g), and potassium carbonate (2.1 g) in N,N-dimethylformamide (15 mL) was stirred under nitrogen gas at 145° C. for 20 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The pooled organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate (Na2SO4) and silica gel (eluted with ethyl acetate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethylacetate=5:1 to 2:1). The 2-[[4-(2-chlorophenyl)-1-piperazinyl]methyl)]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine thus obtained was dissolved in methanol and a stoichiometric excess of 10% hydrogen chloride solution in methanol was added. The mixture was concentrated under reduced pressure and recrystallized from ethanol/diethyl ether to provide 1.0 g of the title compound. Yield 44%.
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