Triethylamine → 5-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2-benzofuran-1(3H)-one

Participants

Reaction Steps

Ozone was bubbled through a solution of 5-allyl-2-benzofuran-1(3H)-one (125 mg, 0.72 mmol) in DCM until the color changed to orange. Removed excess ozone by bubbling nitrogen through solution for a minute. Added a solution of 1-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (65 mg, 0.24 mmol) and triethylamine (0.033 mL, 0.24 mmol) in DCM (2 mL), followed by NaB(OAc)3H (250 mg, 1.2 mmol). The mixture was allowed to stir at RT for 16 hours. HPLC-MS shows product but reaction is not clean. The product was urified by prep-TLC to afford 5-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2-benzofuran-1(3H)-one as a white solid. LC-MS (IE, m/z): 396 [M+1]+. (0.089 μM)

Provenance & Evidence