Synthesis of N-(3-chlorophenyl)-1-adamantanecarboxamide

1-Adamantanecarboxyli acid was synthesized by the reaction of adamantine with formic acid in the presence of concentrated sulfuric acid,and subsequently converted to N-(3-chlorophenyl)-1-adamantanecarboxamide,which was subjected to acylation with an overall yield of about 85.3%.The optimum condition of the third step for the reaction were as follows:the temperature was 130 ℃,the reaction time was 4 h,the molar ratio of 1-adamantanecarboxylic acid,3-chloroaniline and triphenyl phosphate was 1 ∶1 ∶0.6,the solvent volume of dimethylformamide was 50 mL.These compounds were characterized by 1H NMR and IR.