human,TDLo,intramuscular,100ug/kg (0.1mg/kg),SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE,"Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents," National Research Council, 3 vols., Washington, DC, National Academy Press, 1982-85Vol. 1, Pg. L1, 1982.
114 parts of ethyl benzilate, 175 parts of β-diethylaminoethanol and 0.2 part
of metallic sodium were placed in a flask attached to a total-reflux variable
take-off fractionating column. The pressure was reduced to 100 mm and heat
was applied by an oil bath the temperature of which was slowly raised to
90°C. During three hours of heating 17 parts of ethanol distilled (35.5°C).
When the distillation of the ethanol became slow, the bath temperature was
raised to 120°C. When the vapor temperature indicated distillation of the
amino alcohol the take off valve was closed and the mixture was refluxed for
one hour. At the end of this period the vapor temperature had dropped and
two more parts of ethanol were distilled, The remaining aminoalcohol was
slowly distilled for three hours. The pressure was then reduced to 20 mm and
the remainder of the aminoalcohol distilled at 66°C. During the reaction the
color of the solution changed from yellow to deep red. The residue was
dissolved in 500 parts of ether, washed once with dilute brine, and three times
with water, dried over sodium sulfate and finally dried over calcium sulfate.
500 parts of a saturated solution of HCl in absolute ether was added and the
resulting precipitate filtered. Dry HCl gas was passed into the filtrate to a
slight excess and the precipitate again filtered. The combined precipitates
were washed with cold acetone. The 106 parts of product was purified by
recrystallization from acetone as fine white crystals which melt at 177°-
178°C.
