Manufacturing Process
A mixture of 14 g (0.05 mol) of α,α-diphenyl-γ-dimethylaminovaleronitrile, 16
g (0.2 mol) of sodium acetate, 14 g (0.2 mol) of hydroxylamine hydrochloride
and 75 ml of ethyl alcohol was refluxed 18 hours. The mixture was cooled,
poured into water and neutralized with ammonium hydroxide. The heavy
white precipitate solidified on standing. The material was filtered and
recrystallized from isopropanol. After three recrystallizations the
aminopentamide product melted at 177° to 179°C.
The product is often used as the acid sulfate which is produced as follows:
252.0 g (0.85 mol) of α,α-diphenyl-γ-dimethylaminovaleronitrile was dissolved
in one liter of isopropanol, and 70 ml of concentrated sulfuric acid was added
as rapidly as possible. The mixture was heated until clear, then filtered and
diluted with 1,500 ml of anhydrous ethyl acetate. The solution was cooled and
filtered, and the white crystalline product was dried in vacuum over P2O5.
Purification Methods
Crystallise dimevamide from aqueous EtOH. The hydrochloride forms leaflets from EtOH/Et2O with m 190-191o and is deliquescent. The picrate has m 210-211o. It is an antispasmotic. [Moffett et al. J Am Chem Soc 79 4451, 4457 1957, Beckett J Pharm Pharmacol 8 848 1956, Beilstein 14 III 1363, 14 IV 1865.]
