Cyano:pentyl:phenyl-methoxymethyl-oxazolidinone - useful as antidepressant

摘要

3-(4-(5-cyanopentyl)phenyl-5 -methoxymethyl-2 -oxazolidinone of formula (I) is new. The intermediates 3-(4-(5-benzyloxypentyl) phenyl-5 -methoxymethyl-2 -oxazolidinone (II) is also new. (I) is prepd. by treating 3-(4-(5-hydroxypentyl)phenyl-5 -methoxymethyl-2 -oxazolidinone (III) with mesyl chloride in a basic medium and reacting the prod. with an alkali metal cyanide. (I) is an antidepressant with ca. 300 times the reserpine-antagonist activity of toloxatone and with low toxicity (LD50 above 1000 mg/kg, p.o., mouse).