Potential antidepressants: 1-(4-Aminoalkoxy)phenyl)-2-propylamines

Abstract

1-(4-Hydroxyphenyl)-2-propylamine (X) and its N-monomethyl (XI) and N,N-dimethyl (XII) derivatives were O-alkylated with six tert.aminoalkyl chlorides to aminoalkyl ethers Ia-VIc. In cases of X and XI the reactions were complicated by O,N-dialkylation leading to isolation of triamino ethers XVI and XVII. 1-(4-Hydroxyphenyl)propan-2-one was alkylated with 2-dimethylaminoethyl chloride and the ether XIII was obtained. An attempt to transform 4-(2-dimethylaminoethoxy)benzaldehyde to the 1-aryl-2-nitropropene XIV by heating with nitroethane in acetic acid in the presence of ammonium acetate resulted in the formation of 4-(2-dimethylaminoethoxy)benzonitrile (XV). In the form of salts the amino ethers prepared were tested for antidepressant activity but proved little active or inactive.