Abstract The synthesis of 2, 3-dihydrospiro [benzofuran-2, 4′-piperidines] 3 and 2, 3- dihydrospiro [benzofuran-2, 3′]-pyrrolidine] 6 is described. The synthesis was achieved by a Grignard reaction of a 2-fluorobenzylhalide with an appropriate cycloazaalkyl ketone to yield the tertiary alcohols 1 and 4. Subsequent intramolecular displacement of the aromatic fluoride by the derived alkoxides provided the novel system.