adafenoxate

Originator

Adafenoxate ,Laboratorios Wassermann

Manufacturing Process

Preparation of the p-chlorophenoxyacetate of 1-aminoadamantine-2-ethanol, starting from a p-chlorophenoxyacetic acid halide:
22 g (0.11 mol) of 1-aminoadamantine-2-ethanol dissolved in 250 ml of benzene are poured into a 500 ml flask fitted with a mechanical stirrer, using a decanting funnel. 23 g (0.11 m) of p-chlorophenoxyacetyl chloride are added in drops while stirring, the mixture then being stirred for 30 minutes. 120 ml of a 10% solution of sodium carbonate is then added, and the resulting mixture is stirred for 10 minutes. The organic phase is decanted, and the benzene is then removed by distillation. The residue is crystallized with petroleum ether. This yields 37 g (93%) of a white solid.
Preparation of the p-chlorophenoxyacetate of 1-aminoadamantine-2-ethanol, starting from p-chlorophenoxyacetic acid:
In a 1 liter flask, provided with a Dean-Stark separator tube and reflux refrigerant, a mixture of 20.5 g (0.011 m) of p-chlorophenoxyacetic acid, 22 g (0.11 m) of 1-aminoadamantine-2-ethanol, 98 g of conc. sulfuric acid and 700 ml of toluene is heated to boiling point over a period of 24 hours. At the end of this period, the mixture is treated with an aqueous solution of 5% sodium carbonate to an alkali pH, and is then washed with water. The mixture is then dried on anhydrous sodium sulphate, and the toluene is removed by distillation at reduced pressure. The crude product so obtained is crystallized with petroleum ether. The yield is 35.2 g (88%) of a white solid.
Preparation of the chlorhydrate of p-chlorophenoxyacetate of 1- aminoadamantine-2-ethanol:
A solution of 60 g (0.16 m) of p-chlorophenoxyacetate of 1-aminoadamantine- 2-ethanol in 300 ml of ether is subjected to the passage of HCl gas until the precipitation of a solid product is completed. It is left to cool in a refrigerator over a period of 6 hours and it is then filtered. The resulting solid is recrystallized with a mixture of ether and methanol. 61 g (92%) of the product are obtained.

Therapeutic Function

Nootropic, Psychostimulant