Acetic Acid → 3-[2-(4-Bromophenyl)ethoxy]-N-[2-[2-(4-hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-N-phenethyl-propanamide

Participants

Reaction Steps

3-[2-(4-Bromophenyl)ethoxy]-N-(2-oxoethyl)-N-phenethyl-propanamide (Example 10d), 0.54 g) was dissolved in methanol (25 mL) and treated with 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.32 g), acetic acid (0.5 mL) and water (1.5 mL). The resultant mixture was stirred at room temperature for 2 hours and then sodium cyanoborohydride (0.05 g) was added and the reaction mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in methanol (25 mL) and adsorbed onto silica gel. The adsorbed mixture was purified by flash chromatography to yield the titled compound (0.51 g) as a crystalline yellow solid.

Provenance & Evidence