530 
Analogues  of  Atropine. 
f  Am.  Jour.  Pharm. 
I       July,  1 918. 
ate.  This  solution  was  then  shaken  out  with  chloroform  to  re- 
move the  pseudopelletierine,  and  then  made  strongly  alkaline  with 
sodium  hydroxide  solution,  and  the  iso-methylgranatoline  shaken 
out  with  chloroform.  After  being  dried  over  anhydrous  sodium 
sulphate,  the  alkamine  is  obtained  as  a  crystalline  residue  upon  re- 
moving the  chloroform.  It  was  then  recrystallized  from  petroleum 
ether.  The  base  is  readily  soluble  in  water,  alcohol,  and  chloro- 
form, but  less  soluble  in  petroleum  ether.    M.  p.  650  (uncorr.). 
Subst,  0.2515;  N,  20.25  Cc.  at  761  Mm.  and  210  ;  collected  over  30  per 
cent.  KOH  solution. 
Calc.  for  C9H17NO :  N,  9.032  per  cent.    Found :  9.310  per  cent. 
Preparation  of  the  Hydrobromide  of  Tropic  Acid  Ester  of  Iso- 
methylgranatoline. — Three  Gm.  of  iso-methylgranatoline  and  3  Gm. 
of  tropic  acid  were  dissolved  in  10  per  cent,  hydrochloric  acid,  and 
the  mixture  heated  for  70  hours  on  a  water  bath,  the  acid  being  re- 
placed from  time  to  time  as  it  evaporated.  The  mixture  was  then 
diluted  with  water,  and  the  excess  tropic  acid  removed  by  shaking 
out  with  ether.  Ammonia  in  excess  was  then  added  to  the  aqueous 
solution,  and  the  ester  shaken  out  with  a  little  chloroform.  The 
chloroform  solution  was  extracted  then  with  dilute  hydrobromic 
acid,  avoiding  an  excess.  This  aqueous  solution  of  the  hydrobro- 
mide was  evaporated  to  dryness  in  a  vacuum  desiccator  over  cone, 
sulphuric  acid.  The  dry  residue  was  then  recrystallized  from  abso- 
lute, ethyl  alcohol.  It  was  found  necessary  to  repeat  the  recrystalli- 
zation  several  times  to  completely  remove  all  ammonium  bromide. 
The  product  so  obtained  was  a  white  crystalline  powder,  turning 
yellow  upon  prolonged  exposure  to  the  light.  It  is  soluble  in  water 
or  hot  alcohol,  less  so  in  cold  alcohol.    M.  p.  2330  (uncorr.). 
Subst.,  0.3909;  N,  13.20  Cc.  at  757  Mm.  and  260  ;  collected  over  30  per 
cent.  KOH  solution. 
Calc.  for  GsFUNOsBr :  N,  3.64  per  cent.    Found :  3.76  per  cent. 
Preparation  of  the  Hydrobromide  of  the  Mandelic  Acid  Ester 
of  Iso-methylgranatoline. — Three  Gm.  of  iso-methylgranatoline  and 
3  Gm.  of  mandelic  acid  were  dissolved  in  10  per  cent,  hydrochloric 
acid,  and  were  heated  for  70  hours  in  an  evaporating  dish  upon  a 
water  bath.  The  hydrochloric  acid  which  evaporated  was  replaced, 
from  time  to  time,  by  the  addition  of  new  acid.  Only  sufficient  acid 
was  added  to  keep  all  the  reacting  products  in  solution.  At  the  end 
of  the  time  stated,  the  reaction  mass  was  diluted  with  a  little  water , 
