Hydrochloric Acid → 1-[4-(7-Phenyl-3,4-dihydronaphthalene-2-carboxamido)-benzyl]pyridinium chloride

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Reaction Steps

To a mixture of N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (200mg), triethylamine (158 μl) and THF (10ml) was added methane-sulfonic acid anhydride (118mg) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (3ml), and to the mixture was added pyridine (137 μl). The mixture was stirred at room temperature for 96 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)-benzyl]pyridinium chloride (Compound 18) (95mg) as colorless crystals.

Provenance & Evidence