Carlytene,Dedieu,France,1962
A hydrochloric acid solution of 100 g of thymol in alcohol is reacted with 72 g
of sodium nitrite, the nitrosothymol (Organic Syntheses 6, New York, 1926, p.
92) thus obtained is introduced into ammonia, and is reduced by the
introduction of hydrogen sulfide to 4-aminothymol (Organic Syntheses Coll.
Vol. 1, New York, 1932, p. 458). 133.3 g of this 4-aminothymol are mixed
with 67 g of sodium acetate, 107 g of glacial acetic acid and 80 g of acetic
acid anhydride to form 4-acetaminothymol (Plancher, Gazzetta Chimica
Italiana 25, II, p. 388). 156 parts by weight of this last formed substance
dissolved in 600 cc of alcohol are added to a solution of 17.6 parts by weight
of sodium in 600cc of alcohol, the mixture being boiled under reflux for some
time with 82 g of dimethylaminoethyl chloride. The reaction product is treated
with water, and neutralized with hydrochloric acid using acid Congo reagent
indicator, and the alcohol is distilled off in vacuo. The base liberated by alkali
is dissolved in ether. By evaporating the ether solution the dimethylaminoethyl
ether of the 4-acetaminothymol is obtained as a brownish-yellow oil. After
some time this oil solidifies in a crystalline state.
100 g of this base are dissolved in a mixture of 300 cc of concentrated
hydrochloric acid (density 1.19) and 400 cc of water, and the solution is boiled
for one hour under a reflux condenser. Thereupon it is made alkaline,
extracted with ether, and the ether is distilled off. 23.6 g of the 4-
aminothymoxyethyldimethylamine thus obtained are diazotized in the
presence of sulfuric acid at a temperature not exceeding 0°C using a solution
of 7.2 g of sodium nitrite in 70 cc of water, and the diazo compound is heated
to boiling point after the addition of 1 g of copper sulfate, until no further gas
is evolved. It is then made alkaline, and carbon dioxide is introduced. The
base is precipitated first in an oily state, and soon becomes crystalline. The 4-
oxythymoxyethyldimethylamine forms a neutral hydrochloride which is readily
soluble in water, and has a melting point of 174°C to 175.5°C.
36.8 g of 4-oxythymoxyethyldimethylamine are boiled for one hour on a water
bath with 160 cc of acetic anhydride and 17.5 cc of pyridine. After this period,
the solution is diluted with water, made alkaline, and the base is extracted
with ether and the ether distilled off. With acids, the base obtained forms
crystalline salts which are readily soluble in water. The hydrochloride melts
between 208°C and 210°C.
World Health Organization (WHO)
Moxisylyte was introduced in the late 1980s. It belongs to the
group of a-adrenergic blocking agents. In France it is indicated for the treatment of
manifestations of benign prostatic hypertrophy. It is also marketed in the UK at
lower dosages for the treatment of peripheral vascular disorders (Raynaud's
disease).
