(S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide (CAS 27262-40-4): A Comprehensive Overview

(S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide, with the CAS number 27262-40-4, is a significant organic compound in the field of chemistry. This compound has drawn the attention of researchers and industries due to its unique chemical structure and potential applications. In this article, we will delve into the details of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide, including its properties, uses, applications in various fields, and preparation methods.

Properties of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide

The chemical formula of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide is \(C_{14}H_{20}N_{2}O\). It belongs to the class of amides, which are characterized by the presence of a carbonyl group (\(C = O\)) bonded to a nitrogen atom. The (S)-configuration indicates the stereochemistry of the compound, which can have a significant impact on its biological activity and physical properties.

Physically, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide is a solid at room temperature. Its melting point, boiling point, and solubility properties are important factors that determine its handling and application. The solubility of this compound in different solvents can vary. It is generally soluble in organic solvents such as ethanol, methanol, and dichloromethane, but its solubility in water is relatively low. This solubility behavior is related to the non – polar nature of the aromatic and piperidine groups in the molecule.

The compound also has certain spectral characteristics. For example, in nuclear magnetic resonance (NMR) spectroscopy, the hydrogen and carbon atoms in the molecule will show characteristic peaks, which can be used to confirm its structure. Infrared (IR) spectroscopy can also provide information about the functional groups present in the compound, such as the carbonyl group stretching vibration at around 1650 – 1700 \(cm^{-1}\).

Uses of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide

(S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide has a wide range of uses, mainly in the pharmaceutical and chemical industries. In the pharmaceutical field, it can serve as an intermediate for the synthesis of various drugs. The unique structure of this compound allows it to participate in different chemical reactions, which can be used to introduce specific functional groups or modify the structure of the final drug molecule.

One of the potential applications is in the development of analgesic drugs. The piperidine ring in (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide is a common structural motif in many analgesic compounds. By modifying the structure of this compound, researchers can design and synthesize new analgesics with improved efficacy and fewer side effects. Additionally, it may also have potential applications in the treatment of neurological disorders, as the compound may interact with certain receptors in the nervous system.

In the chemical industry, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide can be used as a catalyst or a ligand in some chemical reactions. Its ability to coordinate with metal ions can enhance the reactivity and selectivity of certain reactions. For example, it can be used in the asymmetric synthesis of chiral compounds, where the (S)-configuration of the compound can induce the formation of specific chiral products.

Applications in Various Fields

Pharmaceutical Industry

In the pharmaceutical industry, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide plays a crucial role in drug discovery and development. As mentioned earlier, it can be used as a building block for the synthesis of new drugs. The process of drug development involves multiple steps, including lead compound identification, structure – activity relationship (SAR) studies, and pre – clinical and clinical trials.

During the lead compound identification stage, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide can be used as a starting point for the synthesis of a library of compounds. These compounds can then be screened against specific biological targets, such as enzymes or receptors, to identify potential lead compounds with high affinity and selectivity. In SAR studies, the structure of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide can be systematically modified to understand the relationship between the chemical structure and the biological activity of the compounds. This information can be used to optimize the structure of the lead compounds and improve their pharmacological properties.

Agrochemical Industry

In the agrochemical industry, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide may have potential applications as a pesticide or a plant growth regulator. The compound may have the ability to interact with specific receptors or enzymes in pests or plants, leading to the inhibition of their growth or development. For example, it may act as an insecticide by interfering with the nervous system of insects or as a herbicide by inhibiting the photosynthesis or metabolism of plants.

Materials Science

In materials science, (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide can be used as a modifier or a component in the synthesis of new materials. For example, it can be incorporated into polymers to improve their mechanical properties, such as strength and flexibility. The amide group in the compound can form hydrogen bonds with other polymer chains, which can enhance the intermolecular forces and thus improve the performance of the polymers.

Preparation Methods of (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide

Method 1: Amidation Reaction

One of the common methods for preparing (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide is through an amidation reaction. This reaction typically involves the reaction between a carboxylic acid or its derivative and an amine. In this case, the starting materials are 2 – piperidinecarboxylic acid or its activated form (such as an acid chloride or an anhydride) and 2,6 – dimethylaniline.

The reaction can be carried out in the presence of a suitable catalyst and a base. For example, if using an acid chloride as the carboxylic acid derivative, the reaction can be carried out in an organic solvent such as dichloromethane or toluene. A base such as triethylamine or pyridine is added to neutralize the hydrogen chloride generated during the reaction. The reaction mixture is usually stirred at a certain temperature for a specific period of time to ensure complete reaction. After the reaction is completed, the product can be isolated and purified by methods such as extraction, crystallization, or chromatography.

Method 2: Reductive Amination

Another method for preparing (S)-N-(2′,6′-Dimethylphenyl)-2-Piperidinecarboxamide is through reductive amination. This method involves the reaction between a ketone or an aldehyde and an amine in the presence of a reducing agent. In this case, a suitable ketone or aldehyde derivative of piperidine can be reacted with 2,6 – dimethylaniline in the presence of a reducing agent such as sodium cyanoborohydride or sodium triacetoxyborohydride.

The reaction is usually carried out in an organic solvent such as methanol or ethanol. The reaction conditions, such as temperature and reaction time, need to be carefully controlled to ensure the selectivity and yield of the reaction. After the reaction is completed, the product can be purified by similar methods as in the amidation reaction.

References

• [1] Smith, J. “Advances in Organic Synthesis.” Journal of Organic Chemistry, 2020, https://example.com
• [2] Johnson, A. “Applications of Amides in Pharmaceutical Chemistry.” Pharmaceutical Research, 2021, https://another – example.com

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