Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

Participants

Reaction Conditions

Reaction Steps

5.85 g of 2-(3,5-dimethylpiperidino)-nicotinic acid (prepared from 2-chloronicotinic acid and 3,5-dimethylpiperidine) were dissolved in 25 ml of dimethylformamide. After the addition of 10.41 g of 1-hydroxybenzotriazole (32.4%), 6.5 g of 4-(2-aminoethyl)-2-methoxybenzoic acid ethyl ester . hydrochloride, 6.92 ml of triethylamine and 6.18 g of dicyclohexylcarbodiimide the mixture was stirred for 30 minutes at 50° C. and left to stand overnight at room temperature. Dicyclohexylurea obtained was suction-filtered and washed with 25 ml of dimethylformamide. The combined filtrates were poured into 250 ml of ice-water. Extraction three times with 100 ml of ethyl acetate each time, washing of the acetic ester phase with sodium dicarbonate solution and water and concentration in vacuo gave the ethyl 4-(2-<2-(3,5-dimethylpiperidino)-pyridine-3-carboxamido>ethyl)-2-methoxybenzoate.

Provenance & Evidence