Process for the preparation of n-arylmorpholinones

Abstract

Process for the preparation of compounds of the formula (I) in which X has the meaning indicated in Patent Claim 1 , and precursors thereof.

1 .- 14 . (canceled) 
   
   
       15 . A compound of the formula III
 in which   
     
       
         
         
             
             
         
       
       X denotes 
     
     
       
         
         
             
             
         
       
       R 1  denotes NO 2  or CN, 
       R 2  denotes H, Hal, A, OR 3 , N(R 3 ) 2 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 CON(R 3 ) 2 , NR 3 COOR 3 , NR 3 SO 2 A, —[C(R 5 ) 2 ] n —Ar, —[C(R 5 ) 2 ] n —Het, —[C(R 5 ) 2 ] n -cycloalkyl, COR S , SO 2 N(R 3 ) 2  or SO 2 R 4 , 
       R 3  denotes H, A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het, 
       R 4  denotes A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het, 
       R 5  denotes H or A′, 
       Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OR 5 , N(R 5 ) 2 , NO 2 , CN, COOR S , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR S , SO 2 N(R 5 ) 2  or S(O) n A, 
       Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms which is unsubstituted or mono- or disubstituted by Hal, A, OR 5 , N(R 5 ) 2 , NO 2 , CN, COOR 5 , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR S , SO 2 N(R 5 ) 2 , S(O) n A and/or carbonyl oxygen (═O), 
       A′ denotes unbranched or branched alkyl having 1-6 C atoms, 
       A denotes unbranched, branched or cyclic alkyl having 1-12 C atoms, in which one or two CH 2  groups may be replaced by O or S atoms and/or by —CH═CH— groups and/or in addition 1-7H atoms may be replaced by F, 
       Hal denotes F, Cl, Br or I, 
       n denotes 0, 1 or 2, 
       m denotes 0, 1, 2, 3 or 4, 
       or a salt thereof. 
     
   
   
       16 . A compound according to  claim 15  in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A,   or a salt thereof.   
   
   
       17 . A compound according to  claim 15 , in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A,   R 3  denotes H, A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het,   or a salt thereof.   
   
   
       18 . A compound according to  claim 15  in which
 Ar denotes phenyl,   or a salt thereof.   
   
   
       19 . A compound according to  claim 15  in which
 R 4  denotes A,   or a salt thereof.   
   
   
       20 . A compound according to  claim 15  in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A′,   R 3  denotes H, A′ or —[C(R 5 ) 2 ] n —Ar,   Ar denotes phenyl,   R 5  denotes H or A′,   A′ denotes unbranched or branched alkyl having 1-6 C atoms,   Hal denotes F, Cl, Br or I,   n denotes 0, 1 or 2,   m denotes 0, 1 or 2,   or a salt thereof.   
   
   
       21 . A compound according to  claim 20  in which
 R 1  denotes NO 2 ,   R 2  denotes H, Hal or A′,   R 3  denotes H, A′ or —[C(R 5 ) 2 ] n —Ar,   Ar denotes phenyl,   R 5  denotes H or A′,   A′ denotes unbranched or branched alkyl having 1-6 C atoms,   Hal denotes F, Cl, Br or I,   n denotes 0, 1 or 2,   m denotes 0, 1 or 2,   or a salt thereof.   
   
   
       22 . A process for the preparation of a compound of the formula III 
     
       
         
         
             
             
         
       
       in which 
       X denotes 
     
     
       
         
         
             
             
         
       
       R 1  denotes NO 2 , CN, COOR 3 , CON(R 3 ) 2 , COR 3 , SO 2 R 4 , SO 2 N(R 3 ) 2 , CF 3 , F or Cl, 
       R 2  denotes H, Hal, A, OR 3 , N(R 3 ) 2 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 CON(R 3 ) 2 , NR 3 COOR 3 , NR 3 SO 2 A, —[C(R 5 ) 2 ] n —Ar, —[C(R 5 ) 2 ] n —Het, —[C(R 5 ) 2 ] n -cycloalkyl, COR 3 , SO 2 N(R 3 ) 2  or SO 2 R 4 , 
       R 3  denotes H, A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het, 
       R 4  denotes A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het, 
       R 5  denotes H or A′, 
       Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OR S , N(R 5 ) 2 , NO 2 , CN, COOR S , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR S , SO 2 N(R 5 ) 2  or S(O) n A, 
       Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms which is unsubstituted or mono- or disubstituted by Hal, A, OR 5 , N(R 5 ) 2 , NO 2 , CN, COOR 5 , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR S , SO 2 N(R 5 ) 2 , S(O) n A and/or carbonyl oxygen (═O), 
       A′ denotes unbranched or branched alkyl having 1-6 C atoms, 
       A denotes unbranched, branched or cyclic alkyl having 1-12 C atoms, in which one or two CH 2  groups may be replaced by O or S atoms and/or by —CH═CH— groups and/or in addition 1-7H atoms may be replaced by F, 
       Hal denotes F, Cl, Br or I, 
       n denotes 0, 1 or 2, 
       m denotes 0, 1, 2, 3 or 4, 
       and salts thereof, characterised in that 
       a) a compound of the formula II
   X—NH 2   II 
 
       in which 
       X has the meaning indicated above, 
       is reacted with 5-chloro-2,3-dihydro-1,4-dioxin 
     
     
       
         
         
             
             
         
       
       and 
       the compound of the formula III is optionally converted into its salt. 
     
   
   
       23 . A process according to  claim 22  for the preparation of a compound of the formula III in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal, A, OR 3 , N(R 3 ) 2 , NO 2 , CN, COOR S , CON(R 3 ) 2 , NR 3 COA, NR 3 CON(R 3 ) 2 , NR 3 COOR 3 , NR 3 SO 2 A, —[C(R 5 ) 2 ] n —Ar, —[C(R 5 ) 2 ] n —Het, —[C(R 5 ) 2 ] n -cycloalkyl, COR S , SO 2 N(R 3 ) 2  or SO 2 R 4 ,   R 3  denotes H, A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het,   R 4  denotes A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het,   R 5  denotes H or A′,   Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OR 5 , N(R 5 ) 2 , NO 2 , CN, COOR 5 , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR 5 , SO 2 N(R 5 ) 2  or S(O) n A,   Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms which is unsubstituted or mono- or disubstituted by Hal, A, OR 5 , N(R 5 ) 2 , NO 2 , CN, COOR 5 , CON(R 5 ) 2 , NR 5 COA, NR 5 SO 2 A, COR 5 , SO 2 N(R 5 ) 2 , S(O) n A and/or carbonyl oxygen (═O),   A′ denotes unbranched or branched alkyl having 1-6 C atoms,   A denotes unbranched, branched or cyclic alkyl having 1-12 C atoms, in which one or two CH 2  groups may be replaced by O or S atoms and/or by —CH═CH— groups and/or in addition 1-7H atoms may be replaced by F,   Hal denotes F, Cl, Br or I,   n denotes 0, 1 or 2,   m denotes 0, 1, 2, 3 or 4.   
   
   
       24 . A process according to  claim 23  for the preparation of a compound of the formula III in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A.   
   
   
       25 . A process according to  claim 23  for the preparation of a compound of the formula III in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A,   R 3  denotes H, A, —[C(R 5 ) 2 ] n —Ar or —[C(R 5 ) 2 ] n —Het.   
   
   
       26 . A process according to  claim 23  for the preparation of a compound of the formula III in which
 Ar denotes phenyl.   
   
   
       27 . A process according to  claim 23  for the preparation of a compound of the formula III in which
 R 4  denotes A.   
   
   
       28 . A process according to  claim 23  for the preparation of a compound of the formula III in which
 R 1  denotes NO 2  or CN,   R 2  denotes H, Hal or A′,   R 3  denotes H, A′ or —[C(R 5 ) 2 ] n —Ar,   Ar denotes phenyl,   R 5  denotes H or A′,   A′ denotes unbranched or branched alkyl having 1-6 C atoms,   Hal denotes F, Cl, Br or I,   n denotes 0, 1 or 2,   m denotes 0, 1 or 2.