3 Dimethylaminoethanol HYDROCHLORIDE

By the etherification of succinic acid chloroanhydride with dimethylaminoethanol hydrochloride in the presence of sodium hydroxide succinylcholine was prepared. Then the obtained succinylcholine was purified. To the succinylcholine the methylchloride was added (1 2 mols) and the succinylcholine dichloride was obtained as white powder. 

Synonyms 2-dimethylaminoethyl 4- -butylaminobenzoate hydrochloride 4-(butylamino)benzoic acid 2-(dimethylamino)ethyl ester hydrochloride Amethocaine hydrochloride Anethaine Butethanol Curtacain Decicain Gingicain M Menonasal p-butylamino-benzoyl-2-dimethylaminoethanol hydrochloride Pantocaine Pontocaine hydrochloride Tonexol 4-(butylamino) benzoic acid 2-(dimethylamino)ethyl ester monohydrochloride Uses used as topical and local anesthetic Cross amylocaine hydrochloride A... 

Equimolecular quantities of 4-butylaminobenzoic acid and the hydrochloride of p-dimethylaminoethanol are suspended in 10 times their joint weight of toluene. The mixture is saturated with hydrochloric acid gas and heated in an oil bath at about 150°C while a current of hydrochloric acid, gas is slowly passed through the mixture so that toluene slowly distils. Along with toluene the water produced by the esterification distils. After heating for about 10 hours the mixture is cooled and water is added until the salt is dissolved. The layer of toluene is separated and the ester base precipitated from the aqueous solution by means of a solution of sodium carbonate. By dissolving the base in ether, drying the ether solution separated over potassium carbonate and adding alcoholic hydrochloric acid, to the solution until it is neutral to litmus, the monohydrochloride is obtained in the form of a colorless crystalline powder which, when recrystallized from alcohol, melts at 147-148°C. 

Erythrophlamine crystallizes from ethei hexane and melts at 149-151° with [a] —62.5° (ethanol). The bisulfate, the hydrochloride, the hydrobromide, and the perchlorate are amorphous, but the picrate crystallizes from dilute ethanol and melts at 184-187°. Acid hydrolysis converts this alkaloid into erythrophlamic acid, C21H30O6 (m.p. 218-220°, [a] —63° in ethanol methyl ester, m.p. 177—178°) and dimethylaminoethanol. The... 

Cassamine crystallizes from pentane and then melts at 86-87° with [a]p —56° (ethanol). The perchlorate crystallizes from dilute acetone, the bisulfate from ethanol-ether, and the hydrochloride from acetone, but the salts do not have sharp melting points. The hydrobromide and the picrate were obtained in the amorphous state. When heated with 2N hydrochloric acid cassamine generates dimethylaminoethanol and cassamic acid, CaiHsoOe, (m.p. 217-218°, [a]D —62° in ethanol). This acid yielded a noncrystalline methyl ester which formed a crystalline p-nitrophenyl-hydrazone (m.p. 227-228") and an oxime (m.p. 96-98°). The p-phenyl-phenacyl ester of cassamic acid crystallizes readily and melts at 127-131°. One methoxyl and a double bond conjugated with the carboxyl are present in the acid, so that the function of only one oxygen remains to be determined. 

---