Pyrrolidine

Pyrrolidine

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Chemical structure of Pyrrolidine

Pyrrolidine is a heterocyclic organic compound with the molecular formula C₄H₉N. It is a five-membered ring containing four carbon atoms and one nitrogen atom. Pyrrolidine is a colorless liquid with a distinct odor and is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals.

History

Pyrrolidine was first synthesized by the German chemist Ludwig Knorr in 1882. He obtained it by reacting γ-aminobutyric acid with acetic anhydride. Knorr named the compound "pyrrolidine" due to its structural similarity to pyrrole, another important heterocyclic compound.

Properties

Pyrrolidine has a boiling point of approximately 87 °C and a melting point of -63 °C. It is highly soluble in water and many organic solvents. The compound is known for its characteristic odor, which is often described as ammonia-like.

Synthesis

Pyrrolidine can be synthesized through various methods. One common approach involves the reaction of a primary amine with a ketone or an aldehyde in the presence of an acid catalyst. Another method involves the reduction of pyrrole using a reducing agent such as sodium borohydride.

Uses

Pyrrolidine finds extensive use in the pharmaceutical industry as a building block for the synthesis of various drugs. It is commonly employed in the production of antipsychotic medications, such as haloperidol and risperidone. Additionally, pyrrolidine derivatives have shown potential as anti-cancer agents and as catalysts in organic reactions.

Safety

Pyrrolidine is considered to be a hazardous substance and should be handled with caution. It can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Proper protective measures, such as gloves and goggles, should be used when working with pyrrolidine.

See also

• Pyrrole
• Heterocyclic compound
• Organic synthesis

External links

• Pyrrolidine on PubChem
• Pyrrolidine on Sigma-Aldrich