This report describes the synthesis of pharmacologically interesting 2,5-substituted piperidines from cis and trans ethyl 1-benzyl-6-cyano-3-piperidinecarboxylate 4. Reduction and p-fluorobenzoylation of 4 led to the primary alcohols 7. The alcohols were transformed into the tosylates 11 which were used in nucleophilic substitution reactions. An oxidation-reductive amination route proceeding via the aldehydes 17 also was investigated. Finally a novel synthesis was developed for the 3,6-diazabicyclo[3.2.2]nonanes.