In the course of the synthesis of some 3,5-disubsatuted piperidine compounds which would also contain the essential requirements for analgesic activity, some Guareschi imides were prepared and their subsequent reduction with lithium aluminum hydride was studied. N AN EFFORT to prepare compounds of types I, I 11, and I11 as potential analgesics, Guareschi imides (IV) were synthesized as model compound intermediates. If lithium aluminum hydride would selectively reduce the imide grouping, then the intermediate dicyanopiperidines (V) could be converted into the desired compounds (I, 11) and total reduction of these imides should yield 111. A review of the literature shows no attempted selective reduction of cyanoimides. Avison and Morrison (1) have successfully reduced ethyl-5-chloro-2-cyano-2-phenylvalerate (VI) to 5-chloro-2-cyano-2-phenyl-l-pentanol (VII) but the lactam (VIII) derived from VII yielded only a mixture of basic products when selective reduction was attempted. The model @,&dialkyldicyanoimides (IV) were prepared using the modified procedure of Benica and Wilson (2) for the Guareschi reaction (3). It was noted that the Guareschi hides are insoluble in ðyl ether and other solvents N-R" N-CHI CN I AR-C& R-alkyl IV Rf-CHsCHzOOC-R,R'-alkyl I1 AR-CsH, R-lkyl R"-H, CHs R'<HsCHzC+ I11 AR-Cd-Is R e l k y l R'-HzNCHz-