New 1-(alkoxyphenylalkyl)-2-imidazolinones, -2-imidazolidinones and -2-pyrimidinonesand their manufacture

The invention comprises compounds of formula wherein Rn represents 1 to 3 methoxy or ethoxy groups or a methylenedioxy group, Alk is a straight-chain alkylene radical having 1 to 3 carbon atoms, with 2 or 3 carbon atoms when Z is -C(R3)=CH-, R1 is a hydrogen atom or an alkyl or alkoxy group having 1 or 2 carbon atoms, R2 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a bond to Z, and Z is one of the groupings -C(R3)=CH-, -CH(R3)-CH2-, -CH=CH-C(R3)- and -C(R3)=CH-CH= in which R3 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and their preparation by (a) treating a compound of formula with an acid, (b) heating a compound of formula with urea or another suitable carbonic acid derivative, (c) hydrogenating a product of any of the above, (d) reacting under acidic conditions a compound of formula with a compound of formula HCO-CH2-COR3 or a functional derivative thereof, or (e) alkylating a heterocyclic nitrogen atom in a product obtained by the above methods. Compounds of formula are prepared by reaction of a salt of a compound of formula with a solution of potassium cyanate. Compounds of formula are prepared by reaction of the appropriate amine with the appropriate chloroaldehyde diethylacetal. The compounds of the invention have tranquilizing activity and may be used in combination with a pharmaceutical carrier.