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3-chloro-6-(4-chloropiperidin-1-yl)pyridazine is an organic compound with the chemical formula C9H11Cl2N3.
It is a yellow to yellow-green solid that is soluble in organic solvents.
This compound is commonly used in various applications in the chemical industry, including as an intermediate in the production of pharmaceuticals, agrochemicals, and other chemical products.
The synthetic routes for 3-chloro-6-(4-chloropiperidin-1-yl)pyridazine can vary depending on the desired yield and purity of the final product.
One common synthetic route for 3-chloro-6-(4-chloropiperidin-1-yl)pyridazine is through the reaction of 6-chloropicolinic acid with 4-chloropiperidine in the presence of a polar protic solvent, such as water or methanol.
The reaction involves the nucleophilic substitution of the piperidine N atom for the chloride ion of the acid, followed by dehydration to form the final product.
This route typically yields a product with a high degree of purity, but requires the preparation of the intermediate 6-chloropicolinic acid.
Another synthetic route for 3-chloro-6-(4-chloropiperidin-1-yl)pyridazine is through the reaction of 4-chloro-6-iodopyridazine with 3-chloropiperidine in the presence of a Lewis acid catalyst, such as iron(III) chloride or aluminum chloride.
The reaction involves the reductive nitridation of the iodide ion of the pyridazine to form the final product.
This route typically yields a lower yield of the product, but does not require the preparation of the intermediate 6-chloropicolinic acid.
Both of these synthetic routes are commonly used in the chemical industry, depending on the specific needs of the application.
In addition to these routes, other synthetic methods have also been reported in the literature, such as the reaction of 4-chloro-6-bromopyridazine with 3-chloropiperidine in the presence of a base, or the reaction of 4-chloro-6-nitropyridazine with 3-chloropiperidine in the presence of a nitrogen source.
The synthetic routes for 3-chloro-6-(4-chloropiperidin-1-yl)pyridazine can significantly impact the cost and efficiency of its production.
For example, the choice of solvent and catalyst can affect the rate of the reaction and the yield of the product.
The use of a polar protic solvent, such as water or methanol, can increase the nucleophilicity of the piperidine N atom and lead to a higher yield of the product.
The use of a Lewis acid catalyst, such as iron(III) chloride or aluminum chloride, can increase the acidity of the system and enhance the reactivity of the iodide ion.
In addition to the choice of solvent and catalyst, the conditions of the reaction can also significantly impact the yield and purity of the final product.
For example, the reaction temperature and time can affect the rate of the reaction and the formation of side products.
The use of a higher temperature can increase the rate of the reaction, but may also lead to the formation of undesired side products.
The use of a longer reaction time can increase the yield of the product, but may also lead to the formation of side products.
Overall, the synthetic routes for 3-chloro-6-(4-chloropiperidin-1-yl)pyridazine can vary depending on the specific needs of the application.
The choice of solvent,