Cyclohexanecarbonyl chloride → N-[(2,2-Dimethoxy)ethyl]-N-(2-pyridyl)cyclohexanecarboxamide

Participants

Reaction Steps

To a solution of 6 g of 2-[(2-pyridyl)amino]acetaldehyde dimethyl acetal (prepared as described in Beilstein E III/IV, 22, 3871) in 40 ml of tetrahydrofuran stirred at 0° C. was added dropwise 13.2 ml of butyl lithium (2.5 M solution in n-hexane) and the resulting mixture was stirred at room temperature for 1 h. Afterwards, to the solution was added dropwise in 5 min 4.46 ml of cyclohexanecarbonyl chloride. Stirring was continued for 5.5h, followed by in vacuo evaporation of the reaction mixture to dryness. The residue was purified by flash chromatography (chloroform-ethyl acetate 7:3) affording 13.3 g of the title compound.

Provenance & Evidence