302 



SCIENCE PROGRESS 



two following formulae may therefore be regarded as repre- 

 senting apomorphine : 



H H 



HO 



HO 



HO 



HO 



H H 



Knorr and Raabe 1 have recently shown that -i/r-apocodeine 

 (obtained by heating a mixture of dry codeine and anhydrous 

 oxalic acid at 150 ) 2 is identical with the 3-methylether of 

 apomorphine prepared by Pschorr, Jaeckel, and Fecht ; and 

 thus apomorphine and -v/r-apocodeine stand in the same rela- 

 tionship to one another as morphine and codeine. 



MORPHOLINE AND ITS DERIVATIVES 



The base morpholine 



HoC 

 H 3 C 



O 



NH 



CH 2 

 CH 2 



is of historical interest in that it was at one time regarded 

 by Knorr as the parent substance of morphine, and in order 

 to test the accuracy of this view he synthetically prepared 

 the base and several of its derivatives and elaborated a 

 general method for their preparation. This consists in 

 splitting off water from diethanolamines (prepared by the 

 condensation of ethylene oxide with amines), by heating with 

 strong sulphuric acid 3 : 



CHo\ NH 3 /CH.,— CH,— OH cone. /CH — CH,\ 



I >o 



CH/ 



Ethylenoxide 



-> HN< 



^CH-CH/ 



Diethanolamine 



OH 



H 2 SO, 



-> HN< 



>0 



CH— CH 



Morpholine 



This method can be varied in two directions : ammonia may 

 may be replaced by various mono-substituted ammonias of 



1 Ber. 41, 3050. 2 Ibid. 40, 3355. 3 Ibid. 30, 909 ; 31, 1070, 1969. 



