Process for the cis-selective catalytic hydrogenation of cyclohexylidenamines
AssigneeCiba Specialty Chemicals Corporation
InventorsHeinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
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Abstract
The invention relates to a process for the cis-selective preparation of cyclic amines of the sertralin type by reductive alkylation of cyclic imines or their precursors and catalytic hydrogenation in the presence of copper-containing catalysts and in the presence of a protic solvent.
Claims10
A process for preparing compounds of the formula
- 16
- in which R1 and R2 are, independently of one another, hydrocarbon radicals and A are substituents and m is an integer from 0 to 4 which defines the number of substituents A, which comprises
- a) hydrogenating a cyclohexylidenamine of the formula:
- 17
- in which n is zero or 1, R1, R2, A and m are as defined above, in the presence of a copper-containing catalyst and in the presence of a protic solvent;
- or
- b) reacting a ketone of the formula:
- 18
- in which R2, A and m are as defined above, with a compound which introduces the group R1—N→(O)n, hydrogenating the imine or nitrone (II) obtainable as an intermediate in the presence of a copper-containing catalyst and in the presence of a protic solvent and isolating the cis compound (I).
A process for preparing compounds of the formula I in which the hydrocarbon radicals R1 or R2 are selected from the group consisting of C1-C20alkyl, C4-C12cycloalkyl, C4-C12cycloalkenyl, C2-C11heterocycloalkyl, carbocyclic C6-C16aryl, C2-C15heteroaryl, carbocyclic C7-C16aralkyl and C2-C15heteroarylalkyl and are substituted by functional groups from the group consisting of amino, C1-C4alkylamino, C1-C4dialkylamino, hydroxy, carboxy and halogen, m is two and A are substituents R3 and R4 which are independently or together saturated aliphatic, cycloaliphatic or heterocycloaliphatic radicals or carbocyclic, heterocyclic or carbocyclic-heterocyclic radicals which may be combined in any way with further radicals of this type or be substituted by functional groups from the group consisting of amino, C1-C4alkylamino, C1-C4dialkylamino, hydroxy, carboxy and halogen, which comprises
- a) carrying out the process variant a) using a correspondingly substituted imine (II) in which m is 2 and R1, R2, R3 and R4 are as defined above, or
- b) carrying out the process variant b) using a correspondingly substituted ketone (II) in which m is 2 and R3 and R4 are as defined above.
A process according to any one of claims 14, wherein the compound (I) is prepared by hydrogenation in the presence of a copper chromite, CuCrBa oxide or CuZnAl oxide catalyst.
The use of a copper-containing catalyst for the cis-selective hydrogenation of cyclic imines.
Dependencies are inferred from the claim text.