Patent GB-599376-A (GB)
Title: Manufacture of aminoalkyl ethers, and of quaternary ammonium compounds formed therefrom
Filed: 1944-09-15
Abstract: Aminoalkyl ethers of the general formula <FORM:0599376/IV/1> where A1 is a cycloaliphatic or aliphatic residue (including unsaturated residues), Y1 is hydrogen or a cycloaliphatic or aliphatic residue, Y2 is an aliphatic or cycloaliphatic residue, and Z an N-disubstituted aminoalkyl residue and corresponding quaternary ammonium compounds are prepared by methods which include etherifying an alcohol of the general formula <FORM:0599376/IV/2> or a functional derivative thereof with an N-disubstituted amino alcohol or a functional derivative thereof.  Possible reactions are the reaction of esters of a -substituted cycloaliphatic or aliphatic alcohols such as the halides with amino alcohols disubstituted at the nitrogen atom in the presence of hydrogen halide binding agents, and the reaction of metal compounds of a -substituted cycloaliphatic or aliphatic alcohols (e.g. the alkali metal with salts) basic substituted reactive alkyl esters. Notably the esters with hydrogen halide acids and aryl sulphonic acids.  Other methods by which the above compounds are prepared are the reaction of esterified a -substituted ethers with secondary or tertiary amines and in the case of ethers containing cycloaliphatic groups by the catalytic hydrogenation of the amino ethers or aralkyl alcohols mentioned in Specification 585,994.  By the action of alkyl halides, alkenyl halides, aryl sulphonic acid esters, dialkyl sulphates or aralkyl halides on the N-disubstituted amino alkyl ethers, the quaternary ammonium compounds are obtained.  In examples: (1) diisobutyl-carbinol is treated with sodamide in benzene and b -chloroethyl-diethylamine is added to give (di-isobutyl-methyl)-(b -diethyl-amino-ethyl)-ether; similar products are obtained from n-butyl-isobutyl-carbinol and n-propyl - isobutyl - carbinol; (2) dicyclohexyl - carbinol is similarly treated to give (dicyclohexyl - methyl) - (b  - diethylamino - ethyl) - ether, the same product is obtained by catalytic hydrogenation of cyclohexyl - phenyl - carbin - diethylaminoethyl-ether and (3) n-propyl-cyclohexyl-carbinol is treated with sodamide in benzene followed by b -chloroethyl-diethylamine to give n - propyl - cyclohexyl - carbin - diethyl -aminoethyl-ether; this is also obtained by catalytic hydrogenation of n-propyl-phenyl-carbin - diethylaminoethyl - ether.  Other compounds which may be prepared by the above processes are specified.  n - Propyl - cyclopentyl - carbin - diethylamino - ethyl ether, n-propyl-cycloheptylcarbin-diethyl-aminoethyl ether, n-propyl-(cyclohexylmethyl)-carbin - diethylaminoethyl ether, cyclohexyl - (cyclohexylmethyl) - carbin - diethylaminoethyl diethylaminoethyl ether and methyl-n-butyl-isobutyl - carbin - diethylaminoethyl ether are also prepared by the action of b -chloroethyl-diethylamine on the corresponding carbinols.  n - Propyl - cycloheptylcarbinol is obtainable from cycloheptyl-magnesium bromide and n-butyraldehyde.  n-Propyl-cyclohexylmethyl-carbinol is obtainable from hexahydrobenzyl-magnesium chloride and n-butyraldehyde.  Cyclohexyl-(cyclohexyl-methyl)-carbinol is obtainable from cyclohexylmethyl - magnesium bromide and cyclohexylaldehyde.