Hydrogenating per:fluoro-alkyl-aniline cpds. to cyclohexyl-amine cpds. - useful as herbicide intermediates

摘要

Cyclohexylamines of formula (I) are new: (R5 = 1-3C alkyl, R6 and R7=H or 1-3C alkyl, n = 1-2, m = 1-3). Method for catalytic hydrogenation of anilines of formula (II) to the corresp. cyclohexylamines (Ia) comprises reaction at 50-200 degrees C under a H2 pressure of 1-210 bar over a catalysts contg. Ru and/or Rh. In the formula R1 = OH, alkyl, cylcoalkyl or alkoxy, R2 = H, alkyl, cycloalkyl, alkylcycloalkyl, hydroxyalkyl alkoxyalkyl or perfluoroalkylcycloalkyl, R3 = H, alkyl or phenyl opt. substd by perfluoroalkyl, n' = 1-8, p = 0-4). (Ia) are intermediates for herbicides. (I) are also intermediates for corresp. amides, carbamoyl chlorides and quaternary ammonium salts useful as, or for making, water-proofing agents for paper. Compared with the method, of DT 2528162, yields are higher, H2 pressure and catalyst requirement lower, Na methoxide is not used, and a solvent is not essential. In an example hydrogenation of 3-CF3-aniline over 5% Ru-on-alumina at 100 bar gave a 96.1% yield of 3-CF3-cyclohexylamine.