GB822506A - 2:3:4:5-tetrahydrobenzazepinium salts - Google Patents

Abstract

The invention comprises the general formula <FORM:0822506/IV (a)/1> wherein R1 and R2 stand for methyl radicals or they may be optionally joined either directly or through an oxygen atom to form, together with the adjacent nitrogen atom, a heterocyclic ring, wherein m stands for an integer from 2 to 6 inclusive and wherein X and Z which may be alike or different, stand for anionic groups, particularly for halogen, methosulphate and monovalent radicals derived from di- or polybasic acids, for example the hydrogen sulphate radical, and the preparation thereof whereby a compound of the general formula <FORM:0822506/IV (a)/2> is reacted with a quaternary salt-forming agent of the formula <FORM:0822506/IV (a)/3> wherein Z is a potential anionic group, but attached covalently to the alkylene chain, and, if desired, reacting the quaternary derivative so obtained with a salt containing a different anion. The quaternization process may be carried out by heating the reactants together in a solvent such as ethanol, acetonitrile, methanol, n- or iso-propanol or b -hydroxyethanol, and salt formation in an inert solvent such as water or aqueous ethanol. In examples: N-methyl-2:3:4:5 - tetrahydro - (3-14) - benzazepine is heated with g -bromopropyl-trimethylammonium bromide in ethanol to yield methyl-g -trimethylammonium propyl - 2:3:4:5 - tetrahydro-(3,1H)-benazepinium dibromide, which is treated with silver chloride in aqueous ethanol, the corresponding dichloride. Similarly are prepared methyl d -trimethylammonium butyl-, e - trimethylammonium pentyl-, o - trimethylammonium n - hexyl -, methyl g - (N - methylmorpholinium) - propyl -, g - (N - methylpyrrolidinium) - propyl-, and g - methyl - (N - methylpiperidinium) - propyl - 2:3:4:5 - tetrahydro-(3,1H)-benzazepinium dibromides. The Provisional Specification discloses compounds of the general formula <FORM:0822506/IV (a)/4> wherein R1, R2, R3 and R4 are alkyl radicals which may optionally be substituted for example by hydroxy radicals, or for aralkyl radicals, which may optionally be substituted in the aryl nucleus by, for example, alkoxy groups or by halogen atoms, and wherein R2 and R3 may be joined either directly or through an oxygen atom to form, together with the adjacent N atom, a heterocyclic ring.