302 Canadian Record of Science. 



decide this question, which were suggested to me by Prof. 

 Hofmann of Berlin. 



In the production of this new base, the first step is the 

 preparation of diethyl cumidine. 



For this purpose, carefully dried cumidine hydrochlorate 

 was mixed with somewhat more than the theoretical quan- 

 tity of ethyl alcohol, and the mixture heated in a closed 

 tube to 120°-130° for four hours, when the following re- 

 action — nearly quantitative — occurs : 



C 6 H 2 (CH 3 ) 3 NH 2 , HC1 + 2 C 2 H 6 O = C 6 H 2 (CH 3 ) 3 N (C 2 H 5 ) 2 , 

 H CI + 2 H 2 0. 



Besides the hydrochlorate of the ethylated cumidine, the 

 product was invariably found to contain some ether. Ex- 

 cess of alkali, added to the contents of the tubes, caused 

 he ethylated cumidine to rise with the ether to the surface, 

 whence they could be easily removed and separated. Dis- 

 tillation very readily removes the ether and water, leaving 

 the basic residue which comes over between 220°-230°. 



It is worthy of note that this method of ethylating 

 yielded better results than the usual one of digesting the 

 base with a haloid ether and then separating the secondary 

 base by excess of alkali ; moreover, the employment of the 

 more expensive alcoholic iodide is thus avoided. 



The ethylated cumidine, again sealed up in tubes with 

 about an equal weight of ethyl iodide, is now heated to a 

 temperature of between 280° and 300° for 8 or 10 hours. 

 If the operation be successful, the tubes on cooling con- 

 tain a dark jelly-like mass that cannot be poured out. This 

 consists of the hydriodide of the new base mixed with other 

 bases, a small quantity of some fluid, aromatic hydro- 

 carbons and a tarry residue. 



The hydrocarbons are driven over by steam, and the 

 residue filtered and treated with caustic potash, when there 

 rises to the top a thick reddish, strongly basic oil. 



This oil is separated and fractionated ; the greater part 

 distils over between 285° and 290 ; this is retained and 

 treated with hydrochloric acid. There is formed at once a 

 very insoluble hydrochlorate, crystallising in groups of 



