2-Dimethylaminopyridine → 4-Methyl-1-piperidinecarboxylic acid 2-dibenzofuranyl ester

Participants

Reaction Steps

A mixture of 2-hydroxydibenzofuran (10.0 g, 54.3 mmol), dimethylaminopyridine (DMAP) (7.3 g, 59.8 mmol) and 4-methyl-1-piperidinecarbonyl chloride (8.8 ml, 59.7 mmol) in 200 mL of benzene was refluxed under nitrogen for 7 hours. The reaction was extracted with 1N HCl and then the organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give 17.51 g of a light brown solid. Recrystallization of the solid from diisopropyl ether gave 10.82 g (64%) of the title compound as a light brown crystalline solid, mp 123°-125° C.

Provenance & Evidence