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Compound CAS No. 90000-30-9: (2-Piperidin-3-ylethyl)amine

Introduction to (2-Piperidin-3-ylethyl)amine

Compound CAS No. 90000-30-9, commonly referred to as (2-Piperidin-3-ylethyl)amine, is an organic compound with significant applications in various fields, including pharmaceuticals, agrochemicals, and materials science. This compound belongs to the class of secondary amines and is characterized by its unique structure, which combines a piperidine ring with an ethylamine group. The piperidine ring, a six-membered cyclic amine, contributes to the compound's versatility and reactivity, making it a valuable intermediate in organic synthesis.

Chemical Structure and Properties

The molecular formula of (2-Piperidin-3-ylethyl)amine is C8H16N2. Its structure consists of a piperidine ring (C5H11N) attached to an ethylamine group (-CH2CH2NH2). The compound is a colorless liquid with a faint amine-like odor. It has a molecular weight of 144.21 g/mol and a boiling point of approximately 145°C at standard pressure. The compound is soluble in water and common organic solvents such as ethanol and dichloromethane.

Synthesis and Production

The synthesis of (2-Piperidin-3-ylethyl)amine typically involves the reaction of piperidine with an appropriate alkylating agent, such as ethyl bromide or ethyl chloride, in the presence of a base like sodium hydride or potassium tert-butoxide. This reaction proceeds via an SN2 mechanism, where the nucleophilic amine attacks the electrophilic carbon of the alkylating agent. The reaction conditions are optimized to ensure high yield and purity of the product.

Applications in Pharmaceutical Chemistry

One of the most significant applications of (2-Piperidin-3-ylethyl)amine is in the field of pharmaceutical chemistry. The compound serves as an intermediate in the synthesis of various bioactive molecules, including drugs targeting central nervous system disorders, cardiovascular diseases, and cancer. For instance, it has been used in the development of compounds that modulate GABA receptors, which are critical for treating anxiety and epilepsy.

Recent studies have highlighted the potential of (2-Piperidin-3-ylethyl)amine derivatives as inhibitors of histone deacetylases (HDACs), which are enzymes involved in epigenetic regulation. These derivatives have shown promising results in preclinical models of cancer, suggesting their potential as anticancer agents.

Applications in Agrochemicals

Beyond pharmaceuticals, (2-Piperidin-3-ylethyl)amine finds application in agrochemicals as an intermediate in the synthesis of pesticides and herbicides. Its ability to form stable complexes with metal ions makes it useful in developing formulations that enhance crop protection against pests and diseases.

For example, derivatives of this compound have been investigated for their potential as fungicides targeting plant pathogens such as Fusarium species. These derivatives exhibit high efficacy against fungal infections while maintaining low toxicity to crops.

Applications in Materials Science

In materials science, (2-Piperidin-3-ylethyl)amine is employed as a precursor for synthesizing advanced materials such as polymers and coordination polymers. Its ability to act as a ligand allows it to form stable complexes with metal ions, which can be used to create materials with tailored properties for applications in catalysis, sensing, and drug delivery.

A recent study demonstrated the use of this compound in synthesizing metallopolymers with high thermal stability and mechanical strength. These materials show promise for use in high-performance composites and lightweight structural components.

Environmental Considerations and Safety Profile

As with any chemical compound, understanding the environmental impact and safety profile of (2-Piperidin-3-ylethyl)amine is crucial for its responsible use. The compound is not classified as hazardous under standard conditions but should be handled with care due to its potential irritating effects on skin and eyes.

Eco-friendly synthesis methods for this compound are being explored to minimize its environmental footprint. For instance, researchers are investigating the use of biocatalysts such as enzymes to facilitate its production under mild conditions with reduced energy consumption.

Conclusion

• 61953-28-4(Piperidine, 3,5-dimethyl-, hydrochloride)
• 850350-10-6(PIPERIDINE, 3-[(2S)-2-METHYLBUTYL]-, HYDROCHLORIDE, (3R)-)
• 58531-29-6(3-Methylpiperidine hydrochloride)
• 165288-10-8(1,4-Butanediamine, N1,N4-bis(4-piperidinylmethyl)-, hydrochloride (1:1))
• 58531-32-1(3-Ethylpiperidine hydrochloride)
• 1210824-96-6(4-(Aminomethyl)piperidine HCl)
• 37087-93-7(cis-3,5-dimethylpiperidine;hydrochloride)
• 67288-91-9(trans-3,5-dimethylpiperidine;hydrochloride)
• 223792-48-1((3R)-3-methylpiperidine hydrochloride)
• 155797-02-7((3S)-3-methylpiperidine hydrochloride)