GB836934A - Phenolic amino compounds - Google Patents

Abstract

The invention comprises a process for the preparation of 2-(N,N - disubstituted - amino)-methyl-4-alkyl phenols of the structure <FORM:0836934/IV (b)/1> (in which the R's are alkyl groups or together form a chain, the ends of which are linked to the N atom, and R1 is an alkyl group of at least 4 carbon atoms), by reduction of the corresponding alkyl-salicyl-disubstituted amides of the structure <FORM:0836934/IV (b)/2> The reduction is preferably carried out by means of lithium aluminium hydride in an anhydrous system; but catalytic hydrogenation may also be employed. In an example, a mixture of 5-n-tetradecylsalicyldimethylamide, dry ether and lithium aluminium hydride is refluxed; and then, after standing overnight, the reaction-mixture is treated with aqueous sodium hydroxide and wet ether. Filtration and evaporation of ether from the filtrate gives 2-dimethylamino-methyl-4-n-tetradecylphenol. This compound together with its salts, is claimed per se. The hydrochloride is prepared by dissolving the free base in methanolic hydrogen chloride, and then allowing the solution to evaporate. This salt has anti-tubercular properties. It is stated that the R groups, in the above formul , can form with the N atom a piperidine or morpholine ring. 5 - n - Tetradecylsalicyldimethylamide is obtained by the action of thionyl chloride, followed by dimethylamine, on 5-n-tetradecylsalicylic acid. 5-n-Tetradecylsalicylic acid is obtained by the reduction of 5-myristoylsalicylic acid with zinc amalgam and aqueous hydrochloric acid. 5-Myristoylsalicylic acid is obtained by the reaction between salicylic acid and myristoyl chloride in the presence of aluminium chloride.