Process for the preparation of 3.7-diazabicyclo[3.3.1] nonane compounds
AssigneeClariant Produkte (Deutschland) GmbH
InventorsMichael Wessling, Barbara Duecker, Nicole Nitschke
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Abstract
The present invention relates to a process for the preparation of 3,7-diazabicyclo[3.3.1]nonane compounds. According to the invention, in a first step, a dicarboxylic acid ester is reacted with a pyridine aldehyde and a primary amine. The piperidone which forms is reacted in a second stage with formaldehyde and a further primary amine. It is essential to the invention that, in the first reaction stage, a C2-C4-alcohol is used as solvent and, in the second reaction stage, a C3-C4-alcohol is used as solvent.
Claims3
A process for preparing 3,7-diazabicyclo[3.3.1]nonane compounds of the formula 1
- where R is hydrogen, hydroxyl, C1-C4 alkyl;
- R1 is C1-C4 alkyl, C6-C10 aryl, pyridinyl-C1-C4-alkyl;
- R2 is C1-C4 alkyl, C6-C10 aryl;
- R3 is C1-C4 alkyl and X is C═O or C(OH)2, by
- (a) reacting a dicarboxylic ester of the formula (2)
- with a pyridinealdehyde of the formula (3)
- and an amine of the formula (4)
- R2—NH2 (4)
- to give a piperidone of the formula (5)
- and
- (b) reacting the piperidones of the formula (5) thus obtained with formaldehyde and an amine of the formula R1—NH2, where R, R1, R2 and R3 are each as defined above, which comprises performing reaction stage (a) in a C2-C4-alcohol and reaction stage (b) in a C3-C4-alcohol, and removing the water of reaction formed by azeotropic distillation.
Dependencies are inferred from the claim text.