Process for the preparation of propargyl-amines

Details Process for the preparation of propargyl-amines Process for the preparation of propargyl-amines

C - Chemistry, Metallurgy

07

C

260/604.9

C07C 209/08 (2006.01)

Patent

CA 1215394

NEW PROCESS FOR THE PREPARATION OF PROPARGYL AMINES A B S T R A C T The invention relates to a new process for the preparation of propargyl ammonium chlorides of the general Formula I Image /I/ by alkaline decomposition of the d-tartarate of the 1-isomer of an amine of the general Formula II Image /II/ and subsequent reaction of the amine of the general Formula II with a halide of the general Formula III X - CH2 - C ? CH /III/ in the presence of an organic solvent, alkali and water /in which general Formulae n is 1 or 0 and X stands for halogen/ which comprises - 2 - reacting the d-tartarate of the 1-isomer of an amine of the general Formula II in aqueous suspension with an alkali, dissolving the base of the general Formula II, thus set free without isolation in a water non-miscible organic solvent and reacting the same in the said phase with a halide of the general Formula III, and thereafter - preferably after separating the aqueous layer - reacting the mixture which contains the amines of the general Formulae II and IV Image /IV/ in the organic phase in the presence of water with an organic acid or a solution which has a pH value of 1.5-6 and consists of an inorganic acid and water, thus dissolving in the two-phase mixture formed the salt of the amine of the general Formula II in the aqueous layer and selectively separating the amine of the general Formula II from the amine of the general Formula IV, and thereafter adding after the separation of the phases hydrogen chloride to the amine of the general Formula IV being in the organic phase and thus precipitating the salt of the general Formula I. The compounds of the general Formula I are known pharmaceutical active ingredients. The advantage of the process of the present invention that it is highly economical and enables the recovery of the starting materials on large scale production too.

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