4-(Aminomethyl)piperidine
[CAS# 7144-05-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 4-(Aminomethyl)piperidine
• Synonyms: piperidin-4-ylmethanamine
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• CAS Registry Number: 7144-05-0
• EC Number: 230-446-3
• SMILES: C1CNCCC1CN

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Melting point: 25 ºC (Expl.)
• Boiling point: 200.0±8.0 ºC 760 mmHg (Calc.)^*, 200 ºC (Expl.)
• Flash point: 78.9 ºC (Calc.)^*, 78 ºC (Expl.)
• Index of refraction: 1.457 (Calc.)^*, 1.49 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	4	H227

• Transport Information: UN 3259

Discovory and Applicatios

4-(Aminomethyl)piperidine is a chemical compound with the molecular formula C6H13N. It belongs to the class of piperidine derivatives, which are cyclic amines that have a wide range of applications in medicinal chemistry and organic synthesis. The structure of 4-(aminomethyl)piperidine consists of a piperidine ring—a six-membered nitrogen-containing ring—where an additional aminomethyl group (-CH2NH2) is attached to the carbon at the 4-position of the piperidine ring. This structural feature contributes significantly to its reactivity and versatility in various chemical reactions.

The compound is typically synthesized by introducing an aminomethyl group into the piperidine ring, a process that involves nucleophilic substitution reactions or other synthetic strategies. The availability of a free amine group in the structure of 4-(aminomethyl)piperidine allows for further functionalization and modifications, making it a valuable building block in the synthesis of more complex molecules.

4-(Aminomethyl)piperidine has become an important intermediate in the pharmaceutical industry. Its application spans several therapeutic areas, particularly in the development of central nervous system (CNS) drugs. The compound has been used in the synthesis of drugs for treating neurological and psychiatric conditions, such as depression, schizophrenia, and anxiety. This is primarily due to its ability to modify receptor interactions and its potential to influence neurotransmitter systems.

One notable area of application for 4-(aminomethyl)piperidine is in the preparation of selective serotonin and norepinephrine reuptake inhibitors (SNRIs), which are commonly prescribed to treat depression and anxiety disorders. The aminomethyl group present in 4-(aminomethyl)piperidine can serve as a critical part of the molecular structure for these drugs, allowing for enhanced selectivity and potency in targeting serotonin and norepinephrine transporters.

In addition to its role in CNS drug development, 4-(aminomethyl)piperidine is also used as a precursor for synthesizing other biologically active molecules. For example, it has been employed in the synthesis of compounds with antipsychotic, analgesic, and anti-inflammatory properties. The versatility of the aminomethyl group enables the introduction of various functional groups or modifications that further tailor the pharmacological properties of the final product.

Moreover, 4-(aminomethyl)piperidine plays a significant role in the synthesis of other piperidine-based compounds. These compounds have been found to exhibit a wide range of biological activities, such as antiviral, antibacterial, and anticancer effects. As a result, 4-(aminomethyl)piperidine continues to be a valuable intermediate in the creation of novel drugs with therapeutic potential across various disease areas.

The compound has also gained attention in the field of agrochemicals. It has been used as a starting material in the synthesis of pesticides and herbicides, benefiting from the reactivity of the piperidine ring and the aminomethyl group. The versatility of 4-(aminomethyl)piperidine in agrochemical synthesis allows for the development of new chemical agents that are effective against specific pests and diseases, while potentially minimizing environmental impact.

Despite its utility, 4-(aminomethyl)piperidine must be handled with caution due to its amine group, which can be reactive under certain conditions. Proper safety protocols must be followed when synthesizing, storing, or working with this compound to prevent accidental exposure or chemical reactions that could lead to undesirable outcomes.

In summary, 4-(aminomethyl)piperidine is an essential compound in organic and medicinal chemistry. Its ability to participate in a variety of chemical reactions, coupled with its application in the synthesis of a wide range of biologically active compounds, makes it an important intermediate in pharmaceutical and agrochemical industries. The compound continues to be a key building block for the development of drugs aimed at treating neurological disorders, as well as for the creation of other therapeutic agents and chemical products. The broad applications and versatility of 4-(aminomethyl)piperidine ensure its continued importance in scientific research and industrial applications.

References

2002. Novel substituted 4-aminomethylpiperidines as potent and selective human beta3-agonists. Part 1: aryloxypropanolaminomethylpiperidines. Bioorganic & Medicinal Chemistry Letters, 12(20).
DOI: 10.1016/s0960-894x(02)00607-8

2002. Novel substituted 4-aminomethylpiperidines as potent and selective human beta3-agonists. Part 2: arylethanolaminomethylpiperidines. Bioorganic & Medicinal Chemistry Letters, 12(20).
DOI: 10.1016/s0960-894x(02)00608-x

2006. Identification of a Novel 4-Aminomethylpiperidine Class of M3 Muscarinic Receptor Antagonists and Structural Insight into Their M3 Selectivity. Journal of Medicinal Chemistry, 49(20).
DOI: 10.1021/jm051205r