GB1117626A - Substituted xylenediols - Google Patents

Abstract

Novel amino - alkyl - xylenediols have the formula <FORM:1117626/C2/1> where R is a di-C1- 6-alkylamino-C1- 6-alkyl, amino - C1- 6 - alkyl, C1- 6 - alkylamino - C1- 6 alkyl radical or a group comprising a heterocyclic ring linked through a nitrogen to a C1- 6 alkyl group; both the R1 radicals are the same and represent H, alkyl, aryl, aralkyl or heterocyclic radicals. The benzene nucleus may contain one or more C1- 6 alkyl, C1- 6 alkoxy, CF3 or halo radicals. The novel compounds in which both R1 radicals are hydrogen are obtained by treating a compound of the formula <FORM:1117626/C2/2> with an alkali metal aluminohydride reducing agent, at ambient temperatures in the presence of an inert organic solvent, and recovering the aminoalkyl xylenediol. The compounds in which both R1 radicals are other than hydrogen are obtained by treating the above starting materials with R1MgBr or R1Li in an inert solvent at a temperature of from ambient temperature to the reflux temperature of the solvent. Organolithium compounds, e.g. p-tolyl-lithium, p - chlorophenyl - lithium, p - fluorophenyl lithium, and m-trifluoromethylphenyl lithium, are obtained by reacting n-butyl-lithium with the correspondingly substituted bromobenzene. o-Tolyl lithium is obtained by heating o-bromotoluene in ether with a lithium dispersion. Pharmaceutical compositions, useful as anti-cholinergic, antipyretic, anti-inflammatory and central nervous system stimulant agents, comprise one of the above aminoalkyl xylene-diols together with a pharmaceutical diluent or carrier in unit dosage form such as a tablet, suspension, solution or suppository.