Originator
Phenbutrazate,Shanghai Lansheng
Uses
Fenbutrazate is a derivative of Phenmetrazine (P314500). Fenbutrazate is a psychostimulant used as an anorexigen (appetite suppressant).
Definition
ChEBI: Fenbutrazate is a member of morpholines.
Manufacturing Process
1105 g of 2-phenyl-3-methyl-4-(α-hydroxyethyl)-tetrahydro-1,4-oxazine-(4-
(2-hydroxyethyl)-3-methyl-2-phenylmorphotine) are dissolved in 4000 ml of
anhydrous toluene. 910 g of α-phenyl-α-ethyl acetic acid chloride (2-ethyl-2-
phenyl-acetylchloride) are dissolved in 400 ml of anhydrous toluene and the
resulting solution is slowly added to the heated solution of the tetrahydro-1,4-
oxazine compound. The mixture is then heated to boiling for about 5 hours.
About 1000 g of ice are added to the cooled reaction mixture, which is then
rendered alkaline by the addition of 20% sodium carbonate solution to a pH of
9.0. Thereafter the mixture is vigorously stirred by means of a turbine mixer
for one hour and the toluene phase is separated. The toluene solution is
washed with 1000 ml of saturated sodium chloride solution and is dried over
anhydrous sodium sulfate. The toluene is then evaporated and the residue is
subjected to high vacuum distillation. 1650 g of α-phenyl-α-ethylacetic acid
(2-phenyl-3-methyltetrahydro-1,4-oxazine)-N-ethyl ester (fenburazate),
boiling at 235°-240°C/0.05 mm are obtained thereby in a yield of 90.5% of
the theoretical yield.
Therapeutic Function
Anorexic, Central stimulant
Synthesis
Phenbutrazate is prepared by condensing Nhydroxyethylphenmetrazine
(R = CH2CH2OH)
with 2-phenylbutyric acid. The N-hydroxyethyl
compound is obtained in the same manner as
phendimetrazine .
