SYNTHESIS AND PROPERTIES OF CYCLOHEXYL AMINES OF PROPARGYL SERIES

The possibility of synthesis of the secondary and tertiary cyclohexylamines of propargyl series by interaction of cyclohexylamine with propargyl bromide in the presence of sodium hydroxide has been studied. It has been established that the synthesized secondary amine undergoes the various chemical reactions – hydrosilylation, diene condensation and addition reactions on reactive centers with formation of new derivatives. In particular, it has been shown that N-prop-2-yn-1-ylcyclohexylamine due to N–H bond undergoes the reaction with acrylonitrile and epichlorohydrin (in the presence of boron trifluoride etherate) forming N-cyanoethyl-N-prop-2-yn-1-ylcyclohexylamine and N-epoxy-N-prop-2-yn-1-ylcyclohexyl-amine, respectively. Under action of 10% aqueous solution of hydrochloric acid N-cyanoethyl-N-prop-2-yn-1-ylcyclohexylamine is subjected to the hydrolysis forming unsaturated carboxylic acid. N-epoxy-N-prop-2-yn-1-ylcyclohexylamine due to oxirane ring in interaction with concentrated sulphuric acid leads to the formation of the corresponding glycol of acetylene series and in the reaction with propargyl alcohol – to the formation of the corresponding ether-alcohol with two terminal acetylene bonds. The prepared compounds have been identified by the methods of IR-spectroscopy and NMR. The control over the course of the reaction was carried out by a method TLC on plates with aluminum oxide in the various systems of solvents, developer – iodine