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With an aim of creating new, high affinity dopaminergic ligands, six different 3- and 4-substituted 1-{2-[5-(1H-benzimidazole-2-thione)]ethyl}piperidines and nine related heterocyclic congeners were synthesized and evaluated for in vitro binding affinity at D₁ and D₂ dopamine receptors. Synaptosomal membranes prepared from fresh bovine caudate nuclei were used as a source of the dopamine receptors. Only 4-[bis-(4-fluorophenyl)methylene]-piperidines, compounds 9e, 10d, and 11d, expressed moderate affinity for the D₁ receptors, while all other compounds were inactive competitors of [³H]SCH 23390. Compounds 9c, 9d, 10c, 11a, and 11c were inactive in the D₂ receptor binding assay, as well. Derivatives of 4-phenylpiperidine (9-11b) and 3-phenyl-piperidine (10a) expressed a moderate to low affinity for the D₂ receptors. However, racemic (±)-1-{2-[5-(1H-benzimidazole-2-thione)]ethyl}-3-phenylpiperidine 9a and its enantiomer (+)-9a behaved as selective, high affinity D₂ receptor ligands, the latter being some four times more active than the racemate.