GB789283A - Alkoxyphenoxy-2-hydroxy-propyl carbamates - Google Patents

Abstract

The invention comprises 3-o-methoxyphenoxy-2-hydroxypropyl carbamate and mono-and di-N-alkyl derivatives thereof, wherein the alkyl groups contain 1-6 carbon atoms, and a process for the preparation of alkoxy-phenoxy-2-hydroxypropyl carbamates by reacting a 3-o-alkoxyphenoxy-1 : 2-propanediol with an equimolecular amount of phosgene, adding an equimolecular amount of an organic tertiary amine base such as pyridine, reacting the chlorocarbonate intermediate with ammonia, ammonium hydroxide or a lower-alkyl amine and separating the carbamate ester from the reaction mixture. The compounds are used therapeutically as muscle relaxants and sedatives. In examples: (1) 3-o-methoxyphenoxy-1 : 2-propanediol is reacted with phosgene in benzene, pyridine is added and, after removal of pyridine hydrochloride, the reaction mixture containing 3 - o - methoxyphenoxy - 2 - hydroxypropyl chlorocarbonate is treated with ammonium hydroxide to give 3 - o - methoxyphenoxy-2-hydroxypropyl carbamate; and (2) the benzene solution of 3 - o - methoxyphenoxy - 2 - hydroxypropyl chlorocarbonate obtained as in (1) is treated with dimethylamine to give N : N - dimethyl - 3 - o - methoxyphenoxy - 2 - hydroxypropyl carbamate. Starting material. Alkoxyphenoxy-1 : 2-propane diols such as 3-o-methoxyphenoxy-1 : 2-propanediol are made by heating the sodium or potassium salt of the alkoxyphenol, e.g. o-methoxyphenol, with glycerol in a non-aqueous solvent.