ES267452A1 - Procedure for the preparation of new derivatives of cyclohexane (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Procedure for the preparation of new cyclohexane derivatives, of formula ** (See formula) ** in which R1 = phenyl, cyclohexyl, or cyclohexenyl, to which effect these radicals can be substituted once or twice by halogen, OH, alkyl with at most 4 carbon atoms, alkoxy with at most 3 atoms, of C, -O- CH2-O- or benzyloxy, R2 = -CN, COOR7,-CH2NHCOOR7 o ** (See formula) ** R3 = H, alkoxy with at most 6 C atoms, alkyl with at most 4 C atoms, benzyl, benzyloxy, aryl radical with at most 8 C atoms, R4 = H, OH, alkoxy with at most 4 C atoms, acyloxy with at most 10 C atoms, to which effect R3 and R4 can also mean together = O, = N-OH, or a cyclic ketal group with at most 4 C atoms, R5 and R6 mean H, alkyl with at most 6 C atoms, hydroxyalkyl with at most 3 C atoms, benzyl or alkyl radicals with at most 7 C atoms which are linked together by CH2, O or N, R7 = alkyl or aralkyl radical with at most 8 C atoms, R8 and R9 = hydrogen, alkyl radicals with at most 4 C atoms, or alkyl radicals with at most 4 C atoms which are linked together by CH2, O or N, as well as its addition salts of acids and quaternary ammonium compounds, characterized in that a) a ketone of formula II disubstituted in position 4 is transposed ** (See formula) ** R1 and R2 have the indicated meaning with formaldehyde and an amine of formula III ** (See formula) ** R5 and R6 have the indicated meaning or because b) is introduced into a ketone of formula IV ** (See formula) ** R1, R2, R5, R6 have the indicated meaning in position 1 the substituents R3 and R4, or because c) the nitrile group of a compound of formula is converted ** (See formula) ** where up to R4 have the meaning indicated ** (See formula) ** by hydrogenation in the aminomethyl group, or in the presence of an amine of formula III, in a substituted aminomethyl group, as well as by optionally replacing one or both hydrogen atoms, of the amino group formed by the radicals R5 and/or R6, or why d) is transformed into a compound of formula VI ** (See formula) ** where R1 to R4 have the indicated meaning and X - OH, CL, o Br Radical X by amination in the group (see formula), or by means of reduction, possibly under intermediate protection of the 1-carbonyl group, in a CH2 group, or by f) a compound of formula I is converted according to methods known per se into its acid addition salt, or its quaternary ammonium compound. (Machine-translation by Google Translate, not legally binding)