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US 6,538,136 B1Granted
Preparation of substituted piperidin-4-ones
AssigneeEli Lilly and Company
InventorsJohn Robert Rizzo, Michael Alexander Staszak, Tony Yantao Zhang
Life of this patent
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Abstract
The present invention provides a novel process for the preparation of substituted piperidine-4-ones useful as intermediates in the preparation of pharmaceuticals.
Claims13
A process for the preparation of a compound of formula I:
- wherein R is hydrogen, C1-C6 alkyl, halo(C1-C6)alkyl, phenyl, benzyl, or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, and CN;
- R1, R2, R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, halo(C1-C6)alkyl, phenyl, or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, C1-C6 alkyl, C1-C6 alkoxy, —S(C1-C6 alkyl), —S(phenyl), halo(C1-C6)alkyl, phenyl, NO2, and CN;
- or the pharmaceutically acceptable salt thereof;
- comprising combining a compound of formula II:
- wherein R1, R2, R3, and R4 are defined as above, a compound of formula III:
- wherein R5 is defined as above, and a compound of formula IV:
- R—NH2 formula IV
- wherein R is defined as above, in the presence of a suitable acid;
- followed by addition of a suitable base and a compound of formula V:
- wherein R6 is defined as above.
7 more elements
A process for the preparation of a compound of formula I:
- wherein R is hydrogen, C1-C6 alkyl, halo(C1-C6)alkyl, phenyl, benzyl, or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, and CN;
- R1, R2, R3, R4, R5 and R6 are each independently hydrogen, C1-C6 alkyl, halo(C1-C6)alkyl, phenyl, or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, C1-C6 alkyl, C1-C6 alkoxy, —S(C1-C6 alkyl), —S(phenyl), halo(C1-C6)alkyl, phenyl, NO2, and CN;
- or the pharmaceutically acceptable salt thereof;
- comprising combining a compound of formula II:
- wherein R1, R2, R3, and R4 are defined as above, a compound of formula III:
- wherein R5 is defined as above, an excess of a compound of formula V:
- wherein R6 is defined as above and R6 is the same as R5, and a compound of formula IV:
- R—NH2 formula IV
- wherein R is defined as above, in the presence of a suitable acid;
- followed by addition of a suitable base.
7 more elements
Dependencies are inferred from the claim text.