[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]=2)=[CH:2]1.[ClH:23]>ClCCl.O1CCOCC1>[ClH:23].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=2)=[CH:2]1To a stirred solution of tert-butyl 4-(benzofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.06 g, 6.88 mmol) in dichloromethane (50 ml) was added at room temperature hydrochloric acid solution (4M in dioxane, 25.8 ml, 103 mmol) and the reaction mixture was allowed to stir for 2 h. The reaction mixture was diluted with dioxane (25 ml), the precipitate was collected by filtration, washed with dioxane and dried to yield 4-(benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride as off-white solid (1.37 g, 85%), MS (ISP) m/z=200.2 [(M+H)−], mp 276° C.
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