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

摘要

547,302. Aminoalkylamino compounds. BERGMAN, E. Nov. 14, 1940, No. 7564/41. [Class 2 (iii)] Compounds of the formula, Ar. NH. CHR 3 . R. NSPR1/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. NO a under substantially neutral conditions in the presence of an amino-aldehyde OCH. R.N. #SPR1/SP R2 or an amino-ketone R 3 . CO. R.N SPR1/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) (γ-diethylamino-α - methylpropyl)-4-methoxyaniline by the hydrogenation of 4-nitroanisole and 4-diethylaminobutanone-2 in the presence of Raney nickel and trimethylamine hydrochloride ; (2) 8-(γ-diethylamino - α - methylbutylamino) - 6 - methoxyquinoline by treating 8-nitro-6-methoxyquinoline and 5-diethylamino-pentanone-2 with hydrogen in the presence of palladium-barium sulphate and either cyclohexyldiethylamine hydrochloride or hydrochloric acid. A list of other products is given, including compounds containing bromo and carboxyl groups. Specification 547,301 is referred'to.