2-Bromopyridine → HCID 13787361, compound

Participants

Reaction Conditions

Reaction Steps

2.1 ml (2.2 10-2 mole) of 2-bromopyridine in solution in 10 ml of tetrahydrofuran (THF) are added dropwise to a solution, cooled to -65° C., of 15.6 ml (2.5 10-2 mole) of n-BuLi and of 20 ml of THF. The mixture is stirred for 1/4 h at -65° C. and then 5.6 g (2 10-2 mole) of 1-benzyl-4-benzoylpiperidine in 20 ml of THF are added dropwise while the temperature is maintained at -65° C. The mixture is allowed to warm up very slowly and is then left overnight. It is heated to the reflux temperature for 2 h and then evaporated to dryness, and the residue is taken up with a mixture of water and ether. The ether phase is washed with water, dried, filtered and evaporated down. Chromatography on silica is carried out (eluent 95/5 CH2Cl2 /MeOH). A product which crystallizes from petroleum ether is collected. M.p.= 142°-143° C.

Provenance & Evidence