Improvements in and relating to the synthesis of aromatic and heterocyclic n-(amino-alkyl) substituted amines

摘要

547,301. Aminoalkylamino compounds. BERGMAN, E. Nov. 14, 1940, No. 7563/41. [Class 2 (iii)] Compounds of the formula Ar. NH. CHR 3 . R. N.SPR1/SP R2 in which R represents an aryl group or a benzopyridine residue, R stands for an aliphatic hydrocarbon chain, R 1 and R 2 signify hydrogen or alkyl groups which latter may form part of an alkylene ring, and R 3 represents hydrogen or alkyl, are prepared by reducing compounds Ar.NH 2 under substantially neutral conditions in the presence of an amino-aldehyde OCH. R. N SPR1/SP R2 or anamino-ketone R 3 . CO. R. NSPR1/SP R2 The reduction is preferably carried out with hydrogen in the presence of such catalysts as palladium, platinum and nickel. Examples describe the preparation of (1) #-diethylaminoethyl-p-anisidine by the hydrogenation of p-anisidine and diethyl-aminoacetaldehyde hydrochloride in the presence of Raney nickel; (2) #-diethylamino-α-methylbutyl-aniline by hydrogenating aniline and 5-diethylaminopentanone-2 in the presence of Raney nickel and trimethylamine hydrochloride; (3) (8- diethylamino-α-methylbutyl)-2-chloraniline by reducing a mixture of 2-chloraniline and 5- diethylamino-pentanone-2 with zinc and an acid ; (4) #-diethylamino-α-methylbutyl-1- naphthylamine by the hydrogenation of 1- naphthylamine and 5-diethylamino-pentanone- 2 in the presence of palladium-barium sulphate and diethylamine hydrochloride. A list of other products is given, including #-diethylaminoethyl-9-aminoacridine, 8-(#-diethylaminoethylamino)-quinoline, and compounds containing chloro and carboxyl groups.