Process for preparing vanillylamine hydrochloride

Abstract

Process for preparing vanillylamine or one of the salts thereof by reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, wherein the reaction is carried out in an inorganic or organic acid as diluent, and subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid.

What is claimed is:  
     
         1 . A process for preparing vanillylamine or a salt thereof comprising: 
 a. reacting vanillin with hydroxylamine or the salt thereof in the presence of an organic salt, which may optionally be produced in situ; and    b. hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic acid or inorganic lo acid or a combination of an organic and inorganic acid;    wherein step (a) is carried out in an inorganic or organic acid as diluent.    
     
     
         2 . The process according to  claim 1 , wherein steps (a) and (b) are carried out in a one-pot process.  
     
     
         3 . The process according to  claim 1 , wherein sodium acetate and glacial acetic acid are used in step (a).  
     
     
         4 . The process according to  claim 1  wherein vanillin is reacted with hydroxylamine hydrochloride in step (a).  
     
     
         5 . The process according to  claim 1  wherein Pd/C or Pt/C is used as catalyst in step (b).  
     
     
         6 . The process according to  claim 1  wherein the hydrogenation in step (b) is carried out in the presence of glacial acetic acid and concentrated hydrochloric acid.  
     
     
         7 . The process according to  claim 1  wherein the reaction temperature in step (a) is 15° C. to 50° C.  
     
     
         8 . The process according to claim I wherein the reaction temperature in step (b) is 0° C. to 70° C.  
     
     
         9 . The process according to  claim 1  wherein the vanillin is used in a molar ratio to hydroxylamine or a salt thereof of 1:2 to 2:1.  
     
     
         10 . A pharmaceutical composition comprising a vanillylamine or a salt thereof obtained by the process according to one of  claims 1  to  9 .  
     
     
         11 . A composition comprising pelargonic acid vanillylamide wherein an intermediate product of the pelargonic acid vanillylamide comprises vanillylamine or a salt thereof obtained by a process according to one of  claims 1  to  9 .