4-Bromobutyronitrile → 4-{3-[(Piperidin-1-yl)methyl]phenoxy}butanenitrile

Participants

Reaction Steps

A solution of 3-(1-piperidinylmethyl)phenol (12.05 g) in dry tetrahydrofuran (50 ml) was added dropwise to a suspension of sodium hydride [from 6.0 g of 50% suspension in oil washed with petroleum ether] in dry tetrahydrofuran (70 ml). The mixture was stirred under reflux for 30 minutes and allowed to cool. 4-Bromobutyronitrile (14.89 g, 10.0 ml) was added to the cool mixture and the mixture so obtained was stirred under reflux for 22 hours. Tetrahydrofuran was evaporated under reduced pressure and the residue was dissolved in water (100 ml). The solution was extracted with ether (3×50 ml), and the aqueous layer was adjusted to pH 9 with K2CO3. The aqueous solution was extracted with chloroform (3×100 ml), the chloroform extracts were dried (K2CO3 and chloroform was removed under reduced pressure to give a pale brown oil, (16.22 g). This oil was purified by column chromatography (Kieselgel 60 70-230 mesh silica) using chloroform as eluant. The fractions containing the desired product were collected and the solvent was evaporated in vacuo to give 4-[3-(1-piperidinylmethyl)phenoxy]butyronitrile as an oil (11.37 g).

Provenance & Evidence