Picolinic acid → HCID 21221047, compound

Participants

Reaction Steps

N,N'-Carbonyl diimidazole (6.58 g) was added to a suspension of pyridine-2-carboxylic acid (5.0 g) in dichloromethane (75 ml) stirring under nitrogen at ambient temperature. Stirring continued until gas evolution had ceased (~2 hours) then N-benzylidene-1-(4-piperidyl)methylamine (8.2 g) was added and the reaction mixture stirred for 18 hours. The solvent was evaporated to give a viscous yellow oil, which was then stirred with aqueous potassium hydrogen sulphate solution (1 M; 200 ml) for 18 hours. The mixture was washed with dichloromethane (2×250 ml) and adjusted to pH 14 with aqueous sodium hydroxide solution (5 M) then extracted with methane (3×250 ml). The combined extracts were dried over magnesium and the the solvent removed in vacuo to give 4-(aminomethyl)-1-(2-pyridylcarbonyl)piperidine (5.2 g) as a viscous yellow oil.

Provenance & Evidence