ChEBI: The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.
To 122 grams (1 mol) of p-hydroxybenzaldehyde in 1 liter of chlorobenzene
were added 66 grams (1.04 mols) of sodium methoxide (85%) and 108 grams
(1 mol) of 2-dimethylaminoethyl chloride. The mixture was stirred and
refluxed for 15 hours, then cooled and the precipitated sodium chloride
filtered off. The filtrate was concentrated at steam temperature under water
vacuum and the residual oil was fractionated in high vacuum, to give 4-(2-
dimethylaminoethoxy)benzaldehyde, BP2.2145°C.
Two teaspoons of Raney nickel catalyst were added to a solution of 65.6
grams (0.34 mol) of 4-(2-dimethylaminoethoxy)benzaldehyde in 300 ml of
10% ammoniacal ethanol. The mixture was hydrogenated at 80°C and a
pressure of 1,000 psi. The catalyst was filtered off, the volatiles were distilled
off and the residual oil was fractionated in high vacuum, to obtain 4-(2-
dimethylaminoethoxy)benzylamine, BP0.3120° to 123°C.
To 9.7 grams (0.05 mol) of 4-(2-dimethylaminoethoxy)benzylamine, dissolved
in 100 ml of acetonitrile, was added all at once 12 grams (0.051 mol) of
3,4,5-trimethoxybenzoyl chloride, dissolved in 75 ml of acetonitrile. The
mixture was stirred and refluxed for 8 hours, and then cooled. The crystalline
solid, which had formed, was filtered off, washed with acetonitrile and
recrystallized from acetonitrile, to give 4-(2-dimethylaminoethoxy)-N-(3,4,5-
trimethoxybenzoyl)benzylamine hydrochloride, MP 185° to 186°C.
