Process for producing paroxetine

Abstract

A process for producing a paroxetine represented by the following formula (4), which comprises reacting an N-alkylpiperidine represented by the following general formula (1) with a haloformic acid ester represented by the general formula (2) to prepare an alkoxycarbonylpiperidine represented by the general formula (3), and hydrolyzing the alkoxycarbonylpiperidine under alkaline conditions: wherein each of R 1 and R 2 is a lower alkyl group, a lower cycloalkyl group, an aralkyl group or C m F 2m+1 (wherein m is an integer of from 1 to 6), and X is a halogen atom.

What is claimed is:  
     
         1 . A process for producing a paroxetine represented by the following formula (4), which comprises reacting an N-alkylpiperidine represented by the following general formula (1) with a haloformic acid ester represented by the general formula (2) to prepare an alkoxycarbonylpiperidine represented by the general formula (3), and hydrolyzing the alkoxycarbonylpiperidine under alkaline conditions:  
       
         
           
           
               
               
           
         
       
       wherein each of R 1  and R 2  is a lower alkyl group, a lower cycloalkyl group, an aralkyl group or C m F 2m+1  (wherein m is an integer of from 1 to 6), and X is a halogen atom.  
     
     
         2 . The process according to  claim 1 , wherein each of R 1  and R 2  is a lower alkyl group.  
     
     
         3 . The process according to  claim 1 , wherein each of R 1  and R 2  is a methyl group or an ethyl group.  
     
     
         4 . The process according to  claim 1 , wherein R 1  is a methyl group, and R 2  is a methyl group or an ethyl group.  
     
     
         5 . The process according to  claim 1 , wherein X is a chlorine atom.  
     
     
         6 . The process according to  claim 1 , wherein each of R 1  and R 2  is a lower alkyl group, and X is a chlorine atom.  
     
     
         7 . The process according to  claim 1 , wherein each of R 1  and R 2  is a methyl group or an ethyl group, and X is a chlorine atom.  
     
     
         8 . The process according to  claim 1 , wherein R 1  is a methyl group, R 2  is a methyl group or an ethyl group, and X is a chlorine atom.  
     
     
         9 . The process according to  claim 1 , wherein the alkoxycarbonylpiperidine represented by the general formula (3) is prepared by reacting the N-alkylpiperidine represented by the general formula (1) with the haloformic acid ester represented by the general formula (2) in the presence of a base.  
     
     
         10 . The process according to  claim 9 , wherein the base is an alkali metal hydride, an alkaline earth metal hydride, or an alkali metal carbonate.  
     
     
         11 . The process according to  claim 9 , wherein the reaction is carried out in a solvent at a temperature of from 10 to 150° C.  
     
     
         12 . The process according to  claim 1 , wherein the alkoxycarbonylpiperidine represented by the general formula (3) is hydrolyzed in a solvent at a temperature of from 10 to 150° C.  
     
     
         13 . An alkoxycarbonylpiperidine represented by the following general formula (3):  
       
         
           
           
               
               
           
         
       
       wherein R 2  is a lower alkyl group, a lower cycloalkyl group, an aralkyl group or C m F 2m+1  (wherein m is an integer of from 1 to 6).  
     
     
         14 . The compound according to  claim 13 , wherein R 2  is a methyl group or an ethyl group.