GB797476A - Amides of trialkoxybenzoic acids - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0797476/IV (b)/1> (wherein R is alkyl of 1 to 4 carbon atoms, R1 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or phenethyl, A is an alkylene radical of 2 to 6 carbon atoms or a phenylene radical which may be substituted by halogen atoms or nitro groups and B is dialkylamino, dicycloalkylamino, diaralkylamino, alkylaralkylamino or a saturated, heterocyclic nitrogen containing ring system which may be alkyl substituted and which is connected to A through a heterocyclic nitrogen atom) and acid-addition salts thereof; and their preparation by reacting a halide, ester or azide of the appropriate trialkoxy-benzoic acid with a compound R1-NH-A-B. They may also be prepared by metallation, e.g. with sodium or lithium amide, of the amide of a trialkoxy-benzoic acid and reaction of the metallated amide with the appropriate tertiary aminoalkyl halide or amino phenyl halide. In examples, the following compounds are prepared by reaction of 3 : 4 : 5-trimethoxy-benzoyl chloride with the appropriate primary or secondary amine: N-(b -morpholinoethyl)-, N-methyl - N - (b - morpholinoethyl)-, N - (5 - di - ethylamino - 2 - pentyl)-, N - benzyl - N - (b -morpholinoethyl)-, N - (g - morpholinopropyl)-, N - (b - piperidimoethyl)-, N - (5 - di - n - propylamino - 1 - pentyl)-, N - ethyl - N - (6 - di - n - hexylamino - 1 - hexyl)-, N - [b - (2 - methylpiperidino) - ethyl]-, N - (b - 1 - pyrrolidinyl)-, N - (n - butyl) - N - (b - 1 - pyrrolidinyl)-, N-[4-(N1 - methyl - 1 - piperazinyl) - butyl]-, N-[b -(2 : 6 - dimethylmorpholino) - ethyl]-, N - (b -di-n - hexylaminoethyl)-, N - (b - benzylmethylaminoethyl)-, N - (p - dimethylaminophenyl)-, N - methyl - N - (p - morpholinophenyl)-, N-benzyl - N - (p - piperidinophenyl)-, N - phen - ethyl - N - [p - (a - pipecolinophenyl)]- N-(3 : 5-dichloro - 4 - dimethylamino - phenyl)-, N-(3 : 5-dinitro - 4 - dimethylamino - phenyl)-, N-(3-chloro - 4 - dimethylamino - phenyl)-, N-(3-nitro - 4 - dimethylamino - phenyl)-, N - (p-morpholinophenyl)- and N-benzyl-N-(p-dimethylaminophenyl) - 3 : 4 : 5 - trimethoxybenzamides, and the corresponding triethoxy- and tri-n-hexyloxy compounds corresponding to the first 15 compounds in the above list. Acid-addition salts of some of the products are described and a list of further salt-forming acids including inorganic acids, organic carboxylic acids, ascorbic acid and 8-chlorotheophylline is given. Starting materials. 3 : 4 : 5-Triethoxy- and -tri-n-hexyloxy benzoyl chlorides are prepared from thionyl chloride and the parent acids which in turn are prepared by alkylation of gallic acid, e.g. with ethyl bromide in sodium hydroxide, followed, if necessary, by saponification of any ester formed. N-(p-aminophenyl)-morpholine is prepared by catalytic hydrogenation of N-(p-nitrosophenyl)-morpholine.