Tyramine → HCID 19363452, compound

Participants

Reaction Steps

3,4-Dihexyloxybenzoic acid (161 mg, 0.5 mmol) and 1-hydroxy-benzotriazole hydrate (45.9 mg, 0.3 mmol, 0.6 eq) were dissolved in DMF (5 ml), and to this solution were successively added 2-(4-hydroxyphenyl)ethylamine (82 mg, 0.6 mmol, 1.2 eq) and WSC hydrochloride (114 mg, 0.6 mmol, 1.2 eq) at room temperature. The mixture was stirred at room temperature for 15 hours. This reaction mixture was poured into ethyl acetate (75 ml), washed with water (5 ml×3) and saturated brine (15 ml). The organic layerwas dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=50/1) to give 3,4-dihexyloxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide (230 mg). The obtained solid was recrystallized from ethyl acetate-hexane to give 3,4-dihexyloxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide (194 mg, 88%) as colorless crystals.

Provenance & Evidence