N,N-Dimethylpiperidin-4-amine
[CAS# 50533-97-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: N,N-Dimethylpiperidin-4-amine
• Synonyms: 4-Dimethylaminopiperidine
• Molecular Formula: C₇H₁₆N₂
• Molecular Weight: 128.21
• CAS Registry Number: 50533-97-6
• EC Number: 256-617-2
• SMILES: CN(C)C1CCNCC1

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 179.7±8.0 ºC 760 mmHg (Calc.)^*, 187 ºC (Expl.)
• Flash point: 63.3±9.4 ºC (Calc.)^*
• Index of refraction: 1.479 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H314
• Precautionary Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

N,N-Dimethylpiperidin-4-amine is a chemical compound that belongs to the class of piperidine derivatives. It consists of a piperidine ring, a six-membered nitrogen-containing heterocycle, where the nitrogen atom at position 4 is bonded to two methyl groups (dimethylamino) and an amine group at position 4. The structure of this compound allows it to interact with a variety of biological targets and chemical systems, making it useful in several fields of research and application, particularly in medicinal chemistry and organic synthesis.

The synthesis of N,N-dimethylpiperidin-4-amine typically involves the alkylation of piperidine with methylating agents such as methyl iodide or dimethyl sulfate. This reaction introduces the two methyl groups onto the nitrogen atom, resulting in the formation of N,N-dimethylpiperidin-4-amine. The product can be isolated and purified through common methods such as recrystallization or chromatography.

N,N-Dimethylpiperidin-4-amine is primarily of interest due to its role as a ligand in various chemical reactions. The amine group at position 4 of the piperidine ring provides a site for coordination to metal centers, and the dimethylamino group can influence the compound's electronic properties, making it a useful reagent in organometallic chemistry. The compound can participate in nucleophilic substitution reactions, which are important in the synthesis of various organic molecules.

In medicinal chemistry, N,N-dimethylpiperidin-4-amine and its derivatives have attracted attention for their potential pharmacological properties. The piperidine scaffold is common in many biologically active compounds, and the introduction of dimethylamino groups can modulate the compound’s interaction with biological receptors or enzymes. For example, compounds with a similar piperidine structure have been found to exhibit activity as neurotransmitter reuptake inhibitors, anesthetics, and enzyme inhibitors. N,N-Dimethylpiperidin-4-amine itself may also have potential activity in modulating central nervous system functions, though its exact pharmacological profile would require further study.

The compound's utility extends beyond medicine and into the realm of organic synthesis, where it can be used as an intermediate for the preparation of more complex organic molecules. It may serve as a building block in the synthesis of other piperidine derivatives, which are themselves valuable in the production of pharmaceutical agents, agrochemicals, and other functionalized compounds.

Additionally, the basic nature of the amine group allows N,N-dimethylpiperidin-4-amine to be used as a nucleophile in synthetic chemistry, reacting with electrophiles to form a variety of products. The dimethylamino group can also act as a weak electron donor, influencing the reactivity of the compound in certain reactions, including those involving electrophilic aromatic substitution or addition reactions.

N,N-Dimethylpiperidin-4-amine has the potential to play a role in the development of new materials, particularly in the design of polymers or materials that require piperidine-based linkages or motifs. The amine group can participate in polymerization reactions, forming materials that could have useful properties for various applications, including in coatings, adhesives, or other high-performance materials.

In summary, N,N-dimethylpiperidin-4-amine is a versatile compound with applications in organic synthesis, medicinal chemistry, and materials science. Its structure, which includes a piperidine ring and a dimethylamino group, gives it the ability to interact with a variety of chemical and biological systems. The compound's properties make it useful as an intermediate in the synthesis of other compounds, a ligand in organometallic chemistry, and a potential pharmacological agent. Its presence in many synthetic routes and its possible biological activity continue to make it an interesting compound for further exploration.

References

1998. Molecular Features Associated with Polyamine Modulation of NMDA Receptors. Journal of Medicinal Chemistry, 41(7).
DOI: 10.1021/jm9707129

2020. Aromatic Hydrogenation under Ambient Conditions. Synfacts, 16(12).
DOI: 10.1055/s-0040-1706558

2024. Synthesis of monomers and polymers containing oligocationic groups. Russian Chemical Bulletin, 73(10).
DOI: 10.1007/s11172-024-4423-3