Triethylamine → HCID 15572448, compound

Participants

Reaction Steps

Triethylamine (2.78 ml; 0.02 moles) and ethyl chloroformate (1.9 ml; 0.02 moles) were added successively to a stirred suspension of 2-methoxy-4-amino-5-chlorobenzoic acid (4.0 g; 0.02 moles) in anhydrous tetrahydrofuran (150 ml) whilst maintaining the temperature between -5° and -10° C. After stirring at this temperature for half an hour, a solution of 1-cyclohexylmethyl-3-methyl-4-aminopiperidine (4.2 g; 0.02 moles) in anhydrous tetrahydrofuran (25 ml) was added and, after stirring for 1 hour at -5° to -10° C., the temperature was allowed overnight to reach room temperature. The solvent of the mixture was removed in vacuo, the residue poured into water, extracted with chloroform and the organic layers washed with water. The chloroformic solution was dried (Na2SO4) and the solvent removed in vacuo to give N-(1-cyclohexylmethyl-3-methylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide (3.5 g), m.p. 173°-176° C.

Provenance & Evidence