Hustazol,Yoshitomi,Japan,1972
The manufacture of a related compound is first described. 28.1 parts of pchloro-benzhydryl bromide are heated to boiling, under reflux and with
stirring, with 50 parts of ethylene chlorohydrin and 5.3 parts of calcined
sodium carbonate. The reaction product is extracted with ether and the
ethereal solution washed with water and dilute hydrochloric acid. The residue
from the solution in ether boils at 134° to 137°C under 0.2 mm pressure and
is p-chloro-benzhydryl-(β-chloroethyl)ether.
28.1 parts of this ether are heated with 12 parts of methylethylamine (100%)
in a sealed tube for 4 hours at 110°C. The product of the reaction is extracted
several times with dilute hydrochloric acid, the acid solution made alkaline, in
the cold, with concentrated caustic soda solution and the base which
separates taken up in ether. The ether extract is washed with concentrated
potassium carbonate solution, evaporated down, and the residue distilled in
vacuo. The product is β-methylethyl aminoethyl p-chlorobenzhydryl ether, BP
152° to 153°C/0.1 mm.
Reaction with dimethylethylamine instead of methylethylamine leads directly
to a quaternary compound, which type of compound can also be obtained by
reacting the tertiary aminoethyl ether with reactive esters
If 18 parts of piperidine are used instead of 12 parts of methylethylamine
then the same procedure results in the formation of p-chloro-benzyhydril-(β-
piperidino-ethyl)ether, boiling at 178° to 180°C under 0.15 mm pressure.
