Patent GB-743676-A (GB)
Title: Diammonium compounds
IPC: C07D295/088
Filed: 1953-04-20
Abstract: The invention comprises compounds of the formula <FORM:0743676/IV(a)/1> wherein R and R1 each represent alkyl groups having 1 to 4 carbon atoms or may together represent the atoms necessary to complete a piperidine, methylpiperidine, pyrrolidine, methylpyrrolidine, morpholine or methylmorpholine ring, R2 represents a benzyl radical which can be substituted by alkyl groups having from 1 to 3 carbon atoms or a methylendioxy group or methoxy or ethoxy groups and/or halogen atoms in the benzene nucleus, m represents an integer from 2 to 4, n represents an integer from 8 to 20 and An\s3 represents a monovalent anion or a normal equivalent of a polyvalent anion.  They are obtained by reacting the corresponding di-tertiary bis-amino-alkoxy-alkane with a benzyl halide of the formula R2Hal or, where R and R1 represent alkyl groups, having 1 to 4 carbon atoms, the appropriate di-tertiary bis-aminoalkoxyalkane (already containing the benzyl groups) is reacted with an alkyl compound of the formula R4Hal, R4-O-SO2-OR4 or Aryl-SO2OR4 wherein R4 represents an alkyl group having from 1 to 4 carbon atoms.  The ditertiary bis-aminoalkoxyalkanes can be prepared by reacting an a ,o -diol of the formula HO-(CH2)n-OH with 2 mols. of a tertiary aminoalkyl halide RR1N(CH2)m-Hal, or by reacting an a ,o -dihalogen alkane with a tertiary aminoalcohol RR1N-(CH2)m-OH or by reacting a bis-(halogenalkoxy)-alkane Hal-(CH2)m-O-(CH2)n-O-(CH2m-Ha with secondary amines of the formula RR1NH.  The bis-halogenalkoxyalkanes used in the last method are obtained by reacting bis-(hydroxyalkoxy)-alkanes with phosphorus halides. Bis-(benzyl-alkylaminoalkoxy)-alkanes can also be obtained by reacting a ,o -alkane diols with 2 mols. of acrylonitrile and subsequent hydrogenation to give bis-(aminoalkoxy)-alkanes which on reaction with benzaldehyde under hydrogenating conditions gives bis-(benzylamino-alkoxy)-alkanes which can then be alkylated.  In products containing Hal-, (O-SO2-O-R)- or (Aryl-SO2O)- ions, these latter can be exchanged for other anions.  In example (1) 1,10-bis - [b  - (dimethyl - benzyl - ammonium)-ethoxy)-decane dichloride is prepared by reacting 1,10-bis-(b -dimethylamino-ethoxy)-decane with benzyl chloride. Similarly prepared are (2) 1,10 - bis - (g  - (dimethylbenzyl - ammonium) - propoxy] - decane dichloride; (3) 1,10-bis - [b  - dimethyl - 4 - methylbenzyl - ammonium) - ethoxy] - decane dibromide; and (4) 1,10 - bis - [b  - (dimethyl - 4 - methoxybenzyl - ammonium) - ethoxy] - decane.  A list is given of similarly prepared compounds comprising compounds of the first formula above, which are bis-ethoxy, propoxy and butoxy derivatives of octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, octadecane and eicosane having various terminal groups selected from benzyl-pyrrolidinium, benzyl-2,5-dimethyl - pyrrolidinium, benzyl - piperidinium, benzyl - 2 - methyl - piperidinium, benzylmorpholinium and benzyl-3,5-dimethyl-morpholinium groups, and ammonium groups having as substituents R and R1 methyl, ethyl and propyl groups, and as the substituent R2 benzyl, 4 - fluorobenzyl, 4 - chlorobenzyl, 4-bromo - benzyl, 3,4 - dichlorobenzyl, 3,4 - dimethoxybenzyl, 2 - methoxybenzyl, 4-methoxybenzyl, 4- ethoxybenzyl, 3,5 - dimethylbenzyl, 4 - isopropylbenzyl, 4 - methylbenzyl and 3,4 - methylenedioxybenzyl radicals.  In example (5) 1,10-bis-(b -bromoethoxy)-decane and N-methyl-3,4-dimethoxybenzylamine are reacted to give 1,10-bis-[b -(methyl - 31,41 - dimethoxybenzylamino)-ethoxy)-decane, which is quaternated by reaction with methyl iodide.  Lists are also given of ditertiary bis-amino-alkoxy-alkanes, substituted benzyl halides (containing substituents in 2, 3 and 4 positions), and of alkyl halides, suitable for use as starting materials.  Reference has been directed by the Comptroller to Specification 690,429.