ES409079A1 - Piperidyl carboxylates - Google Patents

Abstract

Procedure for the preparation of piperidine derivatives having the formula ** (See formula) ** and its salts in which n is 1, 2, 3 or 4; R1 is a monovalent radical and an alkyl radical having 1 to 20 carbon atoms, an alkenyl or alkynyl radical having 3 to 20 carbon atoms, an aralkyl radical having 7 to 12 atoms of carbon or a radical that has the formula ** (See formula) ** in which m is 1, 2 or 3, R4 is a hydrogen, a methyl or phenyl radical, X2 is halogen, cyano, (see formula), -COR5, -CO.OR5, -CO.SR5, -CONR5R6 or -CS.NR5R6, X1, is hydroxyl, halogen, cyano, -OR5, (see formula), where R5 is an alkyl radical having 1 to 20 carbon atoms, an alkenyl radical having 2 to 20 carbon atoms, a cycloalkyl radical having 5 to 12 carbon atoms, an aryl radical having 6 to 11 carbon atoms or an aralkyl radical having 7 to 14 carbon atoms or when R5 is attached to a nitrogen atom, likewise hydrogen, R6 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, or R5 and R6 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring that contains no other heteroatoms or contains one or more other heteroatoms or R1 is an acyl group (see formula) where R7 is hydrogen, an unsubstituted or substituted aliphatic radical having 1 to 20 carbon atoms, an alkenyl radical having 2 to 20 carbon atoms, a cycloaliphatic radical having 5 to 12 atoms carbon, an araliphatic radical having 7 to 14 carbon atoms, an aromatic radical having 6 to 20 carbon atoms, or a heterocyclic radical, or R1 is a carbamoyl or thiocarbamoyl radical having the formula ** (See formula) ** where X3 is -O- or -S-, R8 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, and R9 is hydrogen, an alkyl radical having 1 to 20 carbon atoms, an alkenyl radical having 3 to 20 carbon atoms, a cycloalkyl radical having 5 to 12 carbon atoms, or an aryl radical unsubstituted or substituted having 6 to 12 carbon atoms R2 is an alkyl radical having 1 to 4 carbon atoms, an alkenyl or alkynyl radical having 3 to 20 carbon atoms, a cycloalkyl radical which it has 5 to 12 carbon atoms, an aryl radical having 6 to 11 carbon atoms, or an aralkyl radical having 7 to 9 carbon or hydrogen atoms, and when n is 1, R3 is a monovalent radical, and is an alkyl radical having 1 to 20 carbon atoms, a cycloalkyl radical having 5 to 12 carbon atoms, an alkenyl or alkynyl radical having 3 to 20 carbon atoms, a radical of aralkyl having 7 to 12 carbon atoms or a radical having the formula to ** (See formula) ** where m is 1, 2 or 3, R4 is a hydrogen, a methyl or phenyl radical X2 is halogen, cyano, (see formula), -COR5, -CO.OR5, -CO.SR5 or -CONR5R6, and X1 is hydroxyl, halogen, cyano, -OR5, ** (See formula) ** where R5 is an alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical having from 2 to 20 carbon atoms, a cycloalkyl radical, having from 5 to 12 carbon atoms, an aryl radical which has from 6 to 11 carbon atoms or an aralkyl radical having from 7 to 14 carbon atoms or when R5 is attached to a nitrogen atom, likewise hydrogen and R6 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, or R5 and R6 together with the nitrogen atom to which they are attached forms a 5- or 6-membered ring that contains no other heteroatoms or contains one or more other heteroatoms or R3 is an acyl group (see formula), where R7 is hydrogen, an unsubstituted or substituted aliphatic radical having 1 to 20 carbon atoms, an alkenyl or alkynyl radical having 2 to 20 carbon atoms, a cycloaliphatic radical having 5 to 12 carbon atoms, a araliphatic radical having 7 to 14 carbon atoms, an aromatic radical having 6 to 20 carbon atoms or a heterocyclic radical, or R3 is a carbamoyl or thiocarbamoyl radical having the formula ** (See formula) ** in which X3 is -O- or -S-, R8 is hydrogen or an alkyl radical having 1 to 4 carbon atoms, and R9 is hydrogen, an alkyl radical having 1 to 20 carbon atoms, an alkenyl radical having 3 to 20 carbon atoms, a cycloalkyl radical having 5 to 12 carbon atoms, or an aryl radical unsubstituted or substituted having 6 to 12 carbon atoms, or R3 represents a monovalent group obtained by removing a hydroxyl group from a sulfinic acid, a sulfonic acid, a phosphorous-containing acid or a boric acid, or R3 is an aryl radical or a radical having the formula ** (See formula) ** in which R'1 is hydrogen or R'1 has the same significance as R1; when n is 2, R3 is a bivalent radical and is an alkylene radical having 1 to 20 carbon atoms, an alkenylene radical having 2 to 20 carbon atoms, an alkynylene radical having 2 to 20 carbon atoms, a cycloalkylidene radical having 5 to 12 carbon atoms, an arylene radical having 6 to 14 carbon atoms, an aralkylene radical having 8 to 14 carbon atoms, or an aliphatic diacyl radical, aromatic or heterocyclic, the group -CO- or -CO.CO-, a dicarbamoyl or dithiocarbamoyl, sulfanilic or aliphatic or aromatic sulfonyl radical or a bivalent radical obtained by removing two hydroxyl groups from a disulfonic acid, an acid containing phosphorous or boric acid; when n is 3, R3 is a trivalent radical and is an alkanotryl, arenothryl or arenethyryl-trialkylene radical, an aliphatic or aromatic triacyl radical or an o-phosphoric, o-phosphorous or o-boric acid derived triacyl radical and when n is 4, R3 is a tetravalent radical and is an alkanotetrayl radical or a tetraacyl radical derived from an aromatic or aliphatic tetracarboxylic acid or o-silicic acid, as well as, when n is 2, 3 or 4, ethers, partial carbamoyloxy and thiocarbamoyloxy esters and compounds referred to all the reacted compounds of the formula I, characterized in that it comprises reacting, in the presence of an acid binding agent, a piperidinol having the formula ** (See formula) ** in which R1 and R2 are as defined above with an acid halide having the formula R3 (Hal) n (VI) in which R3 and n are as defined above, and Hal represents a halogen atom. (Machine-translation by Google Translate, not legally binding)