Synthesis of Some Amino-oxy, Biguanidino-oxy and Piperazinyl Deriavatives of Propane via reaction between n-Hydroxyphthalimide and Epichlorohydrin

Abstract

2,3-Epoxypropoxyphthalimide (III) was prepared by condensation of
epichlorohydrin (II) with n-hydroxyphthalimide (I) when refluxed for a
short time in presence of sodium hydride but produced bis-phthalimidoxy-
2-hydroxypropane (IV) when refluxed for a long time. Hydroxy group was
replaced by chlorine and subsequent reaction with N-hydroxyphthalimide
gave triphthalimidoxypropane (VI) derivative. Hydrolysis of 1,2,3-triphthalimidoxypropane
in acidic media produced triamino-oxy trihydrohalide
salt of propane (VII). Condensation of polyarnino-oxy compound with
various para substituted dicyandiamide gave corresponding biguanidinooxy
compounds (VIIIa-b).