Acetic Acid → 1-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

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Reaction Steps

To a stirred solution of 1-(2-oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.454 g, 2.26 mmol) in methanol (30 mL) was added (3R)-1-(6-fluoro-1-naphthyl)-3-methylpiperazine (0.61 g, 2.49 mmol), and the mixture stirred for 10 min. Sodium cyanoborohydride (0.157 g, 2.49 mmol) and acetic acid (0.25 mL) were added and the mixture stirred for 18 h. A further portion of sodium cyanoborohydride (0.20 g) was added and the reaction stirred for 6 h. The mixture was quenched with water, and the solvent removed in vacuo. Water was added and the mixture extracted with chloroform, the organic extracts dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative LC-MS to yield the title compound as a yellow oil.

Provenance & Evidence