Triethylamine → N-methyl-N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide

Participants

Reaction Conditions

Reaction Steps

Triethylamine (4.2 ml; 0.03 moles) and a solution of ethyl chloroformate (2.85 ml; 0.03 moles) in anhydrous tetrahydrofuran (35 ml) were added successively to a solution of 2-methoxy-4-amino-5-chlorobenzoic acid (6.04 g; 0.03 moles) in N,N-dimethylformamide (225 ml) whilst maintaining the temperature at -10° C. After stirring at this temperature for 2 hours, a solution of 1-cyclohexylmethyl-4-methylaminopiperidine (6.15 g; 0.03 moles) in anhydrous tetrahydrofuran (35 ml) was added, and the temperature was allowed overnight to reach room temperature. The mixture was poured into an aqueous solution of sodium bicarbonate, extracted with chloroform and the organic layers washed with water. The chloroformic solution was dried (Na2SO4) and the solvent removed in vacuo to give a solid which was recrystallized from a mixture of ethanol and diethyl ether. N-methyl-N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-amino-5-chlorobenzamide (9.6 g) was obtained.

Provenance & Evidence