| Identification | Back Directory | [Name]
adafenoxate | [CAS]
82168-26-1 | [Synonyms]
adafenoxate
Adafenoxato
(p-Chlorophenoxy)acetic acid 2-(1-adamantylamino)ethyl ester
Acetic acid, 2-(4-chlorophenoxy)-, 2-(tricyclo[3.3.1.13,7]dec-1-ylamino)ethyl ester | [Molecular Formula]
C20H26ClNO3 | [MOL File]
82168-26-1.mol | [Molecular Weight]
363.88 |
| Hazard Information | Back Directory | [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 |
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