Potassium Iodide → HCID 19709987, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N,N-diethyl-4-methoxy-3-(4-pyridinylmethoxy)benzamide (19.0 g), 4-picolylchloride hydrochloride (15.0 g), K2CO3 (60.0 g) and potassium iodide (5.0 g) in DMF (500 mol) was stirred at 80° C. for 2 hours and then heated to 150° C. for 15 minutes. After cooling to room temperature, the mixture was poured into 3 l of water, and extracted twice with ethyl acetate. The combined organic phases were washed with 5% Na2CO3, dried (Na2SO4) and concentrated in vacuo. High performance liquid chromatography (silica gel, eluting with 1:1 heptane:ethyl acetate) afforded 6.5 g of the product which was crystallized from heptane/acetone, m.p. 117°-118° C.

Provenance & Evidence