GB1160218A - Substituted 10-Aminoalkylanthracenes - Google Patents

Abstract

1,160,218. Anthracene derivatives. SMITH KLINE & FRENCH LABORATORIES. 8 Feb., 1967 [14 Feb., 1966], No. 2991/69. Divided out of 1,160,217. Heading C2C. Novel compounds of formula wherein R is H or C 1-4 -alkyl, Y is halogen, C 1-4 - alkyl, CF 3 , alkylthio, CN or dimethylsulphamoyl, A is C 2-4 alkylene and Z is amino or mono- or di-C 1-4 -alkylamino or a monocyclic heterocyclic amino group containing 4-12 carbon atoms, such as morpholino, thiomorpholino, pyrrolidino, piperidino, or piperazino, or piperazino substituted in the 4-position by C 1-4 alkyl, hydroxy-C 1-4 -alkyl, #-acetoxy-C 1-4 -alkyl, or #-hydroxy-alkoxy-C 1-4 -alkyl, and acid addition salts thereof are prepared by reaction of a compound of Formula II or a 9-alkyl derivative thereof with the compound HZ optionally followed by salt formation and/or modification of any 4-piperazine substituent. Compounds of Formula II above are prepared by action of HBr on compounds of Formula III which are themselves prepared by action of CH 3 OAMg Halogen on a compound of Formula IV Compounds of Formula IV are prepared, for example, as follows for 2-trifluoromethyl-10- anthrone which is prepared by reaction of phenyl magnesium bromide with 2-bromo-4- trifluoromethylbenzonitrile to give 2-bromo-4- trifluoromethyl-diphenyl-methane which is reduced to yield 2-bromo-4-trifluoromethyl-diphenylmethane which is reacted first with Mg then with CO 2 to give 2-benzyl-5-trifluoromethylbenzoic acid which is cyclized to give the required anthrone. 9-Alkyl substituted compounds of Formula II above are prepared, for example, by action of HBr on a compound of Formula V which is prepared by action of CH 3 O-A-Mg-halogen on a nitrile of Formula VI Nitriles of Formula VI above are prepared. for example, as follows for 2-(α-methylbenzyl)-5- trifluoromethylbenzonitrile which is prepared by reaction of trimethylsulfoxonium iodide and a strong alkali with 2-bromo-4-trifluoromethylbenzophenone to give 1-phenyl-1-(2-bromo-4- trifluoromethylphenyl)-ethylene oxide which is reduced with a bimetal hydride to give α- phenyl - α - (2 - bromo - 4 - trifluoromethylphenyl)-ethanol which on action of P/Hl gives 2 - (α - methylbenzyl) - 5 - trifluoromethyl - bromobenzene which with cuprous cyanide gives the required nitrile.