Tetrahydrofuran → Benzamide

Participants

Reaction Steps

After cooling N,N-dimethyl-1-phenylethane-1,2-diamine represented by Formula 101 (292 mg, 1.78 mmol, purchased from Alfa Aesar Co.) and triethylamine (0.55 mL, 3.95 mmol) in THF (8 mL) at 0° C. under a nitrogen atmosphere, 4-n-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 (606 mg, 1.98 mmol) prepared in Preparative Example 1 in THF (12 mL) was slowly added to the cooled solution. After agitating the above solution at the same temperature for 30 minutes, this was left alone at room temperature for 18 hours. A precipitate generated during the reaction was filtered and discarded, the remaining solution was diluted using chloroform and washed with a potassium carbonate solution, followed by separation and drying with sodium sulfate. The solvent was removed again under reduced pressure. The obtained vacuum-concentrated mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v) using silica gel (SiO2), resulting in a benzamide compound represented by Formula 19 as a desired product (VVZ-020; 451.3 mg, 52% yield).

Provenance & Evidence