Substituted furfurylamines and tetrahydrofurfurylamines

摘要

The invention comprises tetrahydrofurfurylamines of the formula FORM:0907528/IV (b)/1 (wherein Y is cyclohexyl, 1-phenethyl, 2-phenethyl, naphthylmethyl, phenyl optionally substituted by halogen, lower alkyl or lower alkoxy, or benzyl optionally substituted by halogen, lower alkyl or lower alkoxy, R is hydrogen or lower alkyl and R1 is lower alkyl or benzyl, the word "lower" referring to groups containing at most 6 carbon atoms) and their acid-addition and quaternary ammonium salts, and the corresponding furfurylamines (except those wherein R is lower alkyl) wherein Y may additionally be a benzyloxyphenyl group; the preparation of the tetrahydrofurfurylamines by reduction of the furfurylamines and, if desired, alkylation of the compound obtained wherein R is hydrogen to obtain the compound wherein R is lower alkyl; and the preparation of the furfurylamines by heating a compound of the formula FORM:0907528/IV (b)/2 with a Grignard reagent Y-MgHal and, if desired, alkylating the compound obtained wherein R is hydrogen to obtain the compound wherein R is lower alkyl. Examples are given and the optical resolution of some of the products also is described. A list of salt-forming acids and quaternizing agents (including p-nitrobenzyl chloride) also is provided. The tetrahydrofurfurylamines of the invention are stated to be central nervous system stimulants and may be formulated as tablets or capsules or made up, in salt form, into aqueous or saline solutions.