Manufacturing Process
1,7-Bis-(3-ethoxyphenyl)-3-methylaza-7-cyano-nonadecane:
0.06 mole of 1-cyano-1-(3-methoxyphenyl)tridecane (prepared by phase
transfer-catalyzed alkylation of 3-methoxyphenylacetonitrile with 1-
bromododecane) and 0.06 mole of 1-chloro-4-methylaza-6-(3-
methoxyphenyl)hexane [prepared from N-methyl-β-(3-
methoxyphenyl)ethylamine and 1-bromo-3-chloropropane by a method similar
to that described in Arzneim.-Forsch. 28 (II) (1978), 2048] were dissolved in
100 ml of dry toluene in a three-necked flask provided with a stirrer, dropping
funnel, reflux condenser and thermometer. 9.3 g (0.07 mole) of a 30%
strength suspension of sodium amide in toluene were then added dropwise at
from 100° to 110°C, with stirring, and stirring was continued under reflux for
a further 90 minutes.
The resulting reaction solution was poured into 200 ml of ice water, and the
toluene phase was separated off and washed twice with water. The required
amount of hydrochloric acid was added to the toluene solution, the toluene
was distilled off under reduced pressure and the residue, which remained was
recrystallized from acetone to give 1,7-bis-(2-methoxyphenyl)-3-methylaza-7-
cyanononadecane hydrochloride or α-dodecyl-3-methoxy-α-[3-[[2-(3-
methoxyphenyl)ethyl]methylamino]propyl]benzene-acetonitrile (anipamil);
MP: 60°-69.5°C.
