16 



THE ALUMNI JOURNAL 



b) Proof of the presence of the Piperidin rirg is given by the 

 change of tropin into picolinic acid. This is accomplished as 

 follows: 



CH, 



CH, 



-CH- 



-CH. 



Glacial CH3COOH 

 and HCl 



NCH3 COOH- 



-CH. 



-CH- 

 Tropin. 



CH, 



CH. 



-CII- 



CH 



NCH3 CH 



-CH- 



■CH, 



Tropidin. 



Reduction CH, CH CHg Heating with CHg CH CHg 



I I dry HCl 



CH 



NCH3 CHg 



-CH- 



2 v.*x CHg 



Hydrotropidin. 



NH 



CHg CH- 



CH, 



-CH. 



Norhydrotropidin. 



Distilled CHg— C 



with Zn dust 



H 



// 



CH, 



CH 



w 



CH- 



\ / 



CH— CH 



alpha Ethyl pyridin. 



Oxidized 



HOOC— C CH 



// W 



N CH 



\ / 



CH=CH 



alpha Picolinic acid. 



c) Presence of the Cycloheptane or Suberane ring may be shown 

 by exhaustive methylation when Cycloheptatrien is obtained. 



CH. 



CH. 



-CH- 



-CH. 



CH3I and CHg CH 



-CH. 



NCH3 COOH- 



then AgOH. 



— CH— 

 Tropin. 



CH, — 



-CH. 



CH, 



I /CH3 I 15 



N— CH3 COOH^ ^ 



I \0H I j.^ 



CH CH, " 



Tropin methyl hydrate. 



CH; 



-CH==CH 



I 

 CHOH- 



I 

 -CH CH2 



I 



N (CH's') 



CHsIand CH, 

 then AgOH. I 



1 

 CH, 



-CH==CH 



I 



COOH 



I 

 -CH, 



alpha Methyl tropin. 



-CH- 



I 

 N^CCHj) 



\ 

 OH 



N Methyl tropin Methyl hydrate. 



