[Cl-].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][NH3+:16].C([O-])([O-])=O.[K+].[K+].[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O.[BH4-].[Na+]>CO>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][NH:16][CH2:28][C:24]1[O:23][CH:27]=[CH:26][CH:25]=1To a solution of 2-[(1-chloronaphthalen-2-yl)oxy]ethanaminium chloride (100 mg, 0.39 mmol) in 10 mL of MeOH, K2CO3 (65 mg, 0.47 mmol) was added. After 10 min, 48 μL (0.58 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 1 h at room temperature, added with sodium borohydride (15 mg, 0.39 mmol) and the reaction was allowed to stir for further 2 h at room temperature. The solvent was evaporated under vacuum; the mixture was diluted with 10 mL CH2Cl2 and transferred to a separatory funnel. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to afford 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as a brown oil (63% yield). The oil was left to stir with a 4M HCl dioxane solution for 1 h. The reaction mixture was concentrated under reduce pressure to afford 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanaminium chloride as a white solid.
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