Vol. 60 2 -(4'-Methoxy-a-hydroxybenzyl)-4'-methoxydiphenylcarbinol (XIV).-To 3.5 g. of 2-(4"-methoxybenzoyl)-4'methoxybenzophenone, dissolved in 150 cc. of absolute alcohol, there was added 100 g. of 5% sodium amalgam. After several hours the reaction mixture was heated on a steam-bath for two hours, filtered while hot and the filtrate concentrated to one-half its original volume. Water was added gradually until the solution became turbid, the solution cooled and the crystalline precipitate recrystallized from alcohol; m. p. 139-140°; yield 2.8 g.
Effectiveness compared to procaine hydrochloride in producing infiltration anesthesia was estimated by determining the duration of anesthesia following subcutaneous injection of solutions of the new compounds and procaine hydrochloride at different sites on the abdomen of the 'same guinea pig. Toxicities were determined by subcutaneous injection in white mice. The LD50 values found for the standards were: cocaine hydrochloride, 150 mg./kg.; procaine hydrochloride, 600 mg./kg. Summary The reaction of acid chlorides with the hydro-chlorides of 2-alkylaminoethanols (RNHCH2-CH2OH-HCl), dissolved in a solvent such as chloroform or methylene chloride, has been found to be a satisfactory method for esterifying the aminoalcohols. The formation of amides through reaction with the secondary amino group is effectively blocked by converting the aminoalcohols to salts.The local anesthetic activity of a number of benzoates, p-aminobenzoates and phenylurethans of 2-alkylaminoethanols has been examined.New York, N. Y.
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