2-[2-[4-[2-methyl-3-(10H-phenothiazin-10-yl)propyl]piperazin-1-yl]ethoxy]ethanol

Originator

Esucos,UCB Chemie,W. Germany,1962

Definition

ChEBI: Dixyrazine is a member of phenothiazines.

Manufacturing Process

To a suspension of sodamide in liquid ammonia and made from sodium in liquid ammonia, there is added fractionally and with stirring phenothiazine. After an hour there is added thereto, while maintaining the stirring, 1-chloro- 2-methyl-3-bromopropane, then 700 cc of toluene. The ammonia is then driven off and heating under reflux is carried out for one hour.
After cooling, water is added and the solution then decanted. The toluene phase is then evaporated in vacuo to constant weight. The residue is constituted of 10-(2-methyl-3-chloro-propyl)-phenothiazine containing acertain quantity of phenothiazine which has not reacted. As this product is not readily soluble in petroleum ether, it is possible to eliminate it by extraction by means of this solvent.
By operating in this manner 10-(2-methyl-3-chloro-propyl)phenothiazine is obtained. A mixture of l0-(2-methyl-3-chloro-propyl)phenothiazine and 1-[2- (2-hydroxyethoxy)ethyl]piperazine is then heated at 110°-120°C for 20 hours. After cooling, the reaction product is dissolved in 200 cc of benzene and the solution washed several times with water.
The benzene phase is then extracted by dilute hydrochloric acid. The acid aqueous phase is decanted, it is made distinctly alkaline and then extracted with benzene. The benzene extract is dried and evaporated in vacuo. The condensation product could not be crystallized. It may be converted into the dihydrochloride which, after recrystallization from isopropanol, melts at 192°C.

Therapeutic Function

Tranquilizer