Triethylamine → HCID 18973992, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphoryl azide (0.46 ml) was added dropwise to a stirred suspension of 2-pyridylacetic acid (0.367 g) and triethylamine (0.3 ml) in N,N-dimethylformamide (10 ml) maintained at 0° C. A suspension of 4-[3-(2-benzyloxyphenyl)propyl]benzeneamine hydrochloride (0.75 g) in N,N-dimethylformamide (10 ml) containing triethylamine (0.9 ml) was added rapidly to the reaction mixture. Stirring was continued at ambient temperature for 16 hours and the reaction mixture was concentrated to small volume. The residue was partitioned between water and diethyl ether. The diethyl ether extract was washed once each with saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml) and dried. The gum obtained on removal of the solvent was subjected to chromatography on silica (Merck 9385) eluted with a mixture of ethyl acetate and hexane (1:1 v/v). The gum obtained was triturated with ether at 0° C. to give 4-[3-(2-benzyloxy-phenyl)propyl]-N-(2-pyridylmethylcarbonyl)benzeneamine (m.p. 61°-2° C.; yield 0.63 g 68%).

Provenance & Evidence