The Synthetic Routes of Citalopram

Citalopram is a selective serotonin reuptake inhibitor (SSRI) medication commonly used to treat depression and anxiety disorders.
It is also known by its brand name Celexa.
The chemical synthesis of citalopram involves multiple steps and requires the use of various chemical reagents and catalysts.
In this article, we will discuss the synthetic routes of citalopram, starting from the basic building blocks and ending with the final product.

Step 1: Bromination of p-xylene

The first step in the synthesis of citalopram involves the bromination of p-xylene, which is a colorless liquid with a characteristic sweet odor.
Bromination is a chemical reaction that involves the substitution of bromine atoms for hydrogen atoms in a molecule.
This reaction is carried out using a chemical called N-bromo succinimide (NBS) as the brominating agent.

Step 2: Chlorination of toluene

The next step in the synthesis of citalopram involves the chlorination of toluene, which is a colorless liquid with a characteristic smell similar to that of toluene.
Chlorination is a chemical reaction that involves the substitution of chlorine atoms for hydrogen atoms in a molecule.
This reaction is carried out using a chemical called chloroform as the chlorinating agent.

Step 3: Coupling of the brominated and chlorinated compounds

The brominated and chlorinated compounds obtained from the previous steps are coupled together using a chemical reaction called halogenation.
This reaction involves the formation of a new chemical bond between the bromine and chlorine atoms in the two compounds.
The coupling reaction is carried out using a variety of chemical reagents and catalysts.

Step 4: Dealkylation of citalopram

The final step in the synthesis of citalopram involves the dealkylation of the intermediate compound, which is an alkylated phenylamine.
Dealkylation is a chemical reaction that involves the removal of alkyl groups from a molecule.
This reaction is carried out using a chemical called hydrogen chloride (HCl) in the presence of a catalyst like palladium on carbon.

Overall, the synthetic routes of citalopram involve a series of chemical reactions that require the use of various chemical reagents and catalysts.
These reactions are carried out in a step-by-step manner, starting from the basic building blocks and ending with the final product.
The entire process of synthesizing citalopram requires careful control and monitoring of the reaction conditions to ensure the production of a pure and high-quality product.