Patent GB-795988-A (GB)
Title: Alkylene diamines
Filed: 1956-01-19
Abstract: The invention comprises diamines of the general formula <FORM:0795988/IV (b)/1> (wherein R1 and R11 each represent hydrogen, halogen or an alkyl or alkoxy radical, R DEG  represent hydrogen or an alkyl radical of 1-5 carbon atoms, A represents a dialkylamino group or a heterocycloaliphatic group containing a hetero nitrogen atom, n is 0 or 1 and m is 2, 3 or 4) and their acid addition and quaternary ammonium salts; the preparation of the free bases by reacting a haloketone of the formula <FORM:0795988/IV (b)/2> (wherein X represents a halogen) with an alkylene diamine R DEG NH(CH2)mA in the presence of an inorganic base or using excess of the diamine; and the preparation of the acid addition and quaternary ammonium salts by reacting the free bases with acids and with quaternizing agents respectively.  The products are useful therapeutically as local anaesthetics and antifibrillatory agents.  In examples: (1) 1-bromo-1 : 3-diphenyl-2-propanone is allowed to stand with excess of b -diethylaminoethylmethylamine in ether to produce 1-(b -diethylaminoethylmethylamino) - 1 : 3 - diphenyl - 2 - propanone, which is converted into its dihydrochloride by passing dry HCl gas into a solution of the base in ether; similarly prepared are the dihydrochlorides of (2) 1-(b -4-morpholinylethylamino) - 1 : 3 - di - m - tolyl - 2 - propanone, (3) 1 - (b  - 1 - pyrrolidylethylmethylamino) - 1 : 3 - di - o - bromophenyl) - 2 - propanone; (13) 1 - (g  - 1 - piperidylpropylmethylamino) - 1 : 3 - dimethyl-2-propanone; and (14) a -(b -diethylaminoethylamino) - a  - phenyl - p - chloroacetophenone; (4) decyl chloride is allowed to stand with b -diethylaminoethylmethylamine, alkali is added to liberate a -(b -diethylaminoethylmethylamino) - a  - phenylacetophenone, and this is converted to its dihydrochloride as in (1); similarly prepared are the dihydrochlorides of (5) a -(d -4-morpholinylbutylmethylamino)-a -(o - bromophenyl) - o - bromoacetophenone and (6) a  - (b  - 1 - piperidylethylmethylamino) - a  - phenylacetophenone; (7) p : p1-dimethoxydesyl chloride and b -(1-piperidylethyl)-methylamine are allowed to stand with potassium carbonate to produce a -(b -1-piperidylethylmethylamino)-a  - (p - methoxyphenyl) - p - methoxyacetophenone, which is converted to its dihydrogen sulphate by adding conc. H2SO4 to an ethereal solution of the base; similarly prepared is (10) a  - (b  - diethylaminoethylmethylamino) - a  - (p - methoxyphenyl) - p - methoxyacetophenone, which is converted to its dihydrochloride; (8) a -bromobenzyl - p - methylphenyl ketone and b -diethylaminoethylmethylamine are allowed to stand with potassium carbonate in ether to form a  - (b  - diethylaminoethylmethylamino) - a  - phenyl - p - methylacetophenone, which is converted to its dihydrochloride as in (1); similarly prepared are the dihydrochlorides of (9) a -(b -1-piperidylethylmethylamino) - a  - phenyl - p - methylacetophenone; (11) a  - (b  - 1 - piperidylethylmethylamino) - a  - phenyl - p - methylacetophenone, (11) a  - (b  - diethylaminoethylmethylamino) - a  - phenyl - p - chloroacetophenone, and (12) a -(g -1-piperidylpropylmethylamino) - a - phenyl - p - methylacetophenone; (15) and (16) the dihydrochloride products of (4) and (10) respectively are treated with aqueous caustic soda to yield the free bases, which are quaternated with methyl bromide in ether; (17) the product of (1) (free base) is treated with glacial acetic acid in ether to form its acetate.