A series of organoselanyl- and organotellanyl-substituted ethyl- and propylamines and their hydrochlorides, as well as 2-(methylsulfanyl)ethylamine have been synthesized. Efficient general synthetic routes have been developed to chalcogen(S, Se, Te)-containing Schiff bases with di- and trimethylene bridges between the nitrogen atom of the imino group and the chalcogen, by condensation of 3-(tert-butyl)- and 3-(1-ethylpropyl)-2-hydoxybenzene-carbaldehydes with the amines. The influence of the organylchalcogenyl-group on some spectral characteristics (¹H, ¹³C, ⁷⁷Se NMR spectroscopy) of both amines and Schiff bases is discussed.