Methanol → 6-methyl-5-[2-(4-{[4-(1h-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one

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Reaction Steps

To a flask charged with (6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (100 mg, 0.53 mmol) was added 1-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazine hydrochloride (162 mg, 0.53 mmol), sodium cyanoborohydride (165 mg, 2.6 mmol), methanol (10 mL), and a drop of acetic acid. The mixture was allowed to stir at RT for 16 hours. LC showed formation of the desired product. The solvent was removed under reduced pressure. The residue was redissolved in DMSO-water, and purified by mass-directed HPLC. LC/MS: (1E, m/z) (M+1)+=447.3;

Provenance & Evidence