Patent GB-274058-A (GB)
Title: Process for the manufacture of new alkylamino-alkylamino derivatives of aromatic compounds
IPC: C07C209/18
Filed: 1927-06-23
Abstract: 274,058. I. G. Farbenindustrie Akt.- Ges. July 8, 1926, [Convention date]. Addition to 267,169. Alkylaminoalkylamino compounds. - Aminooxycompounds or diamines of the benzene series or their substitution products are converted into more strongly basic polyamino derivatives by the introduction of alkyl amino groups which are joined to the aromatic amino groups through the medium of aliphatic residues. Thus aminophenols or phenylenediamines or their derivatives may be condensed with alkylaminoalkyl halides, or they may be first caused to react with ethylene oxide or halogenated alcohols and the oxyalkylamino compounds so produced be converted into alkylaminoalkylamino compounds. Further, reactive derivatives of the benzene series, for example dioxy compounds or halogen nitro compounds may be condensed with alkylated aliphatic diamines, the nitro groups being subsequently reduced, when present.. Alkylaminoalkylamino benzene compounds containing a further substituent can also be first prepared and the said substituent exchanged for an amino or an oxy group. The preparation of m oxy-N-diethylaminoethylmethyl- and ethylaniline and m - amino - N - diethylaminoethylaniline, which is described and claimed in the parent Specification, is excluded. According to examples the following compounds are obtained :-m-oxy-N-diethylaminoethylaniline from m-aminophenol and diethylaminoethylchloride, or m - oxy-N-methyl-diethylaminoethyl - aniline (described and claimed in the parent Specification) from resorcinol and as-methyl-diethyl-ethylenediamine; m - oxy-N-diethylaminoisoamylaniline from m-aminophenol and alpha-diethylamino-#-chlorpentane ; p - oxy - N - methyldiethylaminoethylaniline from p-methylaminophenol and diethylaminoethylchloride; m - oxy-N-ethyl - dimethylaminoisobutyl-aniline from m-ethylaminophenol and dimethylamino-gamma-chlorbutane; 3-(N-ethyldiethylaminoethyl)-amino-4-methyl - 1 - oxybenzene from 3-ethylamino-4-methyl-1-oxybenzene and diethylaminoethylchloride; and p - amino - N- methyl - diethylaminoethyl-aniline by reducing the corresponding nitroso compound. The products are of therapeutic value having a destructive action on blood parasites. as-Methyldiethylethylenediamine is obtained by alkaline distillation of the p-nitroso compound of N -methyl-diethylaminoethyl-aniline. Dimethylamino-gamma-chlorbutane is obtained by treating dimethylamino-gamma-butanol with thionyl chloride. The Specification as open to inspection under Sect 91 (3) (a) comprises also the conversion of aromatic aminooxy compounds or polyamines in general into more strongly basic polyamino derivatives by the introduction of further amino groups joined to the aromatic amino groups through the medium of aliphatic, hydroaromatic, carbocyclic or heterocyclic residues; the latter may contain free or etherified hydroxyl groups, and the carbon chain may be interrupted by oxygen or sulphur atoms. These compounds may be made by condensing aromatic amino-oxy or polyamino compounds with halogenalkylamines or with corresponding aminoalkyl esters of other inorganic or organic acids, or the basic residues may be introduced by means of phthalimide compounds. The aminooxy or polyamino compounds may also be first caused to react with ethylene oxide or halogenated alcohols and the oxyalkylamino compounds so produced be converted into aminoalkylamino compounds. Aromatic dioxy compounds in general may also be condensed with aliphatic diamines. Aminoalkylamino aromatic compounds containing a further substituent can also be first prepared and the said substituent exchanged for an amino or oxy group; such a substituent may be a nitro, nitroso, azo, acylamino, benzylidine, diazo or sulphonic group. The following additional compounds are obtained in examples :-3 : 4-diethoxy-N-mono- or di- (diethylaminoethyl)-aniline from 3 : 4-diethoxyaniline and diethylaminoethylchloride; 2 : 6-di- (isopropyloxy) - diethylaminoethylaniline; 4: 5-dimethoxy-1: 2-di(diethylaminoethyl)-phenylenediamine; m - amino - N - diethylaminoethyianiline from m-nitraniline and diethylaminoethylchloride followed by reduction' with iron and acetic acid; 1-diethylaminoethylamino-4-methyldiethylaminoethylaminobenzene from 1-amino-4- methyl - diethylaminoethylaminobenzene; 1 - di (diethylaminoethyl) - amino - 4 - dimethylamino-2- methylthiophenol by methylating the SH group of 1-amino-4-dimethylamino-2-thiophenol and condensing with excess of diethylaminoethylchloride; 3-methoxy-4-isopropyloxy - 1 - (diethylaminoethylethyl - amino - ethylamino) benzene (CH3O) (C3H7 O) - C6 H3 - N H - C H2 - C H2 - N (C2 H5)- CH2-CH2-N (C2H5)2 from the parent amine and ethyldiethylaminoethylaminoethyl chloride; the N - (alpha - piperidyl - # - oxy-gamma-propyl)-, N(#<1>-ethyl- # - diethylaminoethylsulphide) - N - (#<1> . ethyl- #-diethylaminoethylether)-, N-(alpha-dimethylaminogamma-ethoxy-#-propyl-, and N- (1-dimethylamino-2- cyclohexyl) derivatives of 1-isopropyloxy-2. methoxy-4-aminobenzene (3 - methoxy-4-isoprop yloxy-1-aminobenzene); 1-mono or di(diethylaminoethyl)-amino-2- : 3 - dimethoxynaphthalene from 1-sulphobenzene-azo-2 : 3-dioxynaphthalene by methylation, reduction to 1-amino-2 : 3-dimethoxynaphthalene, and condensation with diethylaminoethylohloride; 1 - methoxy - 2-diethylaminoethyloxy - 5-diethylaminoethylaminobenzene by condensing the potassium salt of 1-methoxy- 2-oxy-5-nitrobenzene with diethylaminoethylchloride, reducing, and condensing further with diethylaminoethylchloride. This subject-matter does not appear in the Specification as accepted.