2-Fluoropyridine → HCID 20542602, compound

Participants

Reaction Steps

A solution of 4-phenyl-4-piperidinol (7.1 g, 40 mM) in dry DMSO (50 ml) was treated with a 50% sodium hydride dispersion (2.0 g, 40 mM) and the mixture warmed to 80°, until a clear solution was obtained. The solution was cooled to room temperature and treated with a solution of 2-fluoropyridine (3.9 g, 40 mM) in DMSO (10 ml). After 24 hours the reaction mixture was poured onto water (250 ml) and extracted with toluene (3×250 ml). After washing with brine, the organic phase was dried (MgSO4) and the solvents removed under reduced pressure. Recrystallisation from IPE gave the title compound (3.5 g) contaminated with traces of 4-phenyl-4-piperidinol. Fractional crystallisation from cyclohexane gave the title compound analytically pure and chromatographically homogenous (600 mg) m.p. 86°-7°.

Provenance & Evidence