Chloropyramine hydrochloride is a neurotransmitter related agent for research of drug analysis. Also, it is designed to disrupt the focal adhesion kinase (FAK) and vascular endothelial growth factor receptor-3 (VEGFR-3) interaction in neuroblastoma.
A solution comprising 40 parts of 2-bromopyridine, 100 parts of N,N-dimethylN'-(4-chlorobenzyl)ethylenediamine and 100 parts of quinoline is heated at
140-145°C for 5 hours. The oil layer after washing with 30% sodium
hydroxide solution is distilled, and the fraction which distills at 142-170°C/1
mm is collected. This oil is converted to the monohydrochloride and
recrystallized from a mixture of amyl alcohol and ether. The
monohydrochloride salt of N,N-dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)
ethylenediamine is obtained which melts at 167-168.4°C.
N,N-Dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)ethylenediamine may be
prepared by another method:
To a mixture of 100 ml of liquid ammonia and about 80 mg of black iron oxide
was added 0.78 g (0.02 atom) of potassium. When all of the potassium had
reacted, 3.3 g of N,N-dimethyl-N'-(2-pyridyl)ethylenediamine was added. After
the addition of 75 ml of dry toluene the ammonia was removed on the steam
bath. To the cooled and stirred mixture was added 4.26 g of p-chlorobenzyl
chloride, and the reaction mixture was stirred on the steam bath for 11 hours.
It was then filtered and concentrated to an oil. This concentrate was taken up
in ether, and the ethereal solution was washed with water, dried over sodium
sulfate, and concentrated. Distillation gave 2.96 g of yellow liquid. Treatment
of this distillate with an equivalent quantity of hydrogen chloride in absolute
alcohol and precipitation by the addition of anhydrous ether gave 2.33 g of
the N,N-dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)ethylenediamine
hydrochloride.
