302-40-9

Suavitil,Merck Sharp and Dohme,US,1957

ChEBI: 2-hydroxy-2,2-diphenylacetic acid 2-(diethylamino)ethyl ester is a diarylmethane.

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.

Tranquilizer; Anticholinergic