Barnetil,Delagrange,France,1976
ChEBI: Sultopride is a member of salicylamides.
A solution of 17.22 g of N-ethyl-α-aminomethylpyrrolidine in 360 ml of
pyridine is placed in a 1 l balloon flask. A solution of 3.51 g of phosphorus
trichloride in 40 ml of pyridine is added at ambient temperature. After the
mixture has been stirred for 1 hour, 10 g of 2-methoxy-5-ethylsulfonylbenzoic
acid is introduced. The mixture is heated under reflux for 4 ? hours. After
cooling, the solvent is evaporated under vacuum and the residue is dissolved
in 200 ml of 20% sodium hydroxide. The solution is extracted with 200 ml of
chloroform.
The organic solution is dried and filtered and the solvent is evaporated under
vacuum; the residue is dissolved in 150 ml of ethanol and the solution is
acidified with hydrochloric acid. The hydrochloride is dried without heating and
recrystallized from 100 ml of absolute ethanol. 7.2 g of N-(1-ethyl-2-
pyrrolidyl-methyl-2-methoxy-5-ethylsulfonylbenzamide hydrochloride is
produced. Melting point: 190°C to 193°C.
