Am.  Tour.  Pharm.  \ 
July,  19 1 8.  > 
Analogues  of  Atropine. 
531 
and  the  excess  mandelic  acid  removed  by  shaking  out  with  ether. 
The  alkaloid  was  liberated  by  adding  ammonia  water  in  excess  and 
was  then  taken  up  with  a  little  chloroform.  The  hydrobromide  was 
secured  from  this  chloroform  solution  by  shaking  out  with  dil. 
hydrobromic  acid,  and  evaporating  the  aqueous  solution  in  a  vacuum 
desiccator  over  sulphuric  acid.  The  pure  hydrobromide  is  secured 
by  recrystallizing  the  crude  salt  from  absolute  alcohol.  M.  p.  2290 
(uncorr.).  The  salt  is  readily  soluble  in  water  or  hot  alcohol, 
slightly  soluble  in  cold  alcohol. 
Subst,  0.4155 ;  N,  14.50  Cc.  at  763  Mm.  and  250  ;  collected  over  30  per 
cent.  KOH  solution. 
Calc.  for  G-EUNOsBr :  N,  3.78  per  cent.    Found :  3.93  per  cent. 
Preparation  of  the  Hydrobromide  of  the  Tropic  Acid  Ester  of 
Methylgranatoline. — Four  Gm.  of  methylgranatoline  and  4  Gm.  of 
tropic  acid  were  heated  for  70  hours  in  an  evaporating  dish  on  a 
water  bath  with  0.25  per  cent,  hydrochloric  acid.  Sufficient  acid 
was  added  from  time  to  time  to  keep  all  the  reacting  substances  in 
solution.  At  the  end  of  this  time  the  mixture  was  acidified  with 
cone,  hydrochloric  acid,  and  the  unchanged  tropic  acid  removed  with 
ether.  The  aqueous  solution  was  then  made  alkaline  with  ammonia 
water,  and  the  base  taken  up  with  chloroform.  The  hydrobromide 
was  formed  by  extracting  the  alkaloid  from  the  chloroform  by 
shaking  out  with  dilute  hydrobromic  acid.  Upon  evaporating  this 
aqueous  solution  in  a  vacuum  desiccator  over  sulphuric  acid,  the 
crude  hydrobromide  was  secured,  which  was  purified  by  recrystalli- 
zation  from  absolute  alcohol.  M.  p.  2200  (uncorr.).  The  salt  is 
readily  soluble  in  water  and  hot  alcohol,  slightly  soluble  in  cold 
alcohol. 
Subst,  0.4209;  N,  14.10  Cc.  at  759  Mm.  and  200  ;  collected  over  30  per 
cent.  KOH  solution. 
Calc.  for  CisH-cNOsBr :  N,  3.64  per  cent.    Found  :  3.84  per  cent. 
Preparation  of  the  Hydrobromide  of  the  Mandelic  Acid  Ester 
of  Methylgranatoline. — This  compound  was  made  by  heating  4  Gm. 
of  mandelic  acid  and  4  Gm.  of  methylgranatoline  with  0.25  per  cent, 
hydrochloric  acid  in  sufficient  quantity  to  keep  all  the  reacting  sub- 
stances in  solution.  After  heating  for  70  hours,  the  mixture  was 
acidified  with  hydrochloric  acid,  and  excess  mandelic  acid  removed 
by  shaking  out  with  ether.  The  aqueous  solution  was  then  made 
alkaline  with  ammonia  water,  and  the  ester  shaken  out  with  chloro- 
