(R)-3-Methylpiperidine
[CAS# 16078-25-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: (R)-3-Methylpiperidine
• Synonyms: (-)-3-Methylpiperidine; (3R)-3-Methylpiperidine; (R)-(-)-3-Methylpiperidine
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• CAS Registry Number: 16078-25-4
• SMILES: C[C@@H]1CCCNC1

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*
• Boiling point: 125.5 ºC 760 mmHg (Calc.)^*
• Flash point: 17.2 ºC (Calc.)^*
• Index of refraction: 1.422 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(R)-3-Methylpiperidine is an organic compound that belongs to the class of piperidines, which are six-membered heterocyclic compounds containing one nitrogen atom. This specific isomer is a chiral molecule, meaning it has a non-superimposable mirror image, which is crucial in various chemical and pharmaceutical applications. The (R)-configuration refers to the orientation of substituents around the chiral center, which is determined by the Cahn-Ingold-Prelog priority rules.

This compound is commonly synthesized through various methods that typically involve the stereoselective construction of the piperidine ring. One common approach to its synthesis is via reductive amination, where a ketone precursor is reduced in the presence of a suitable amine. The process often uses chiral catalysts or reagents to ensure the formation of the specific (R)-enantiomer, as the (S)-enantiomer may have different properties and activities.

In the pharmaceutical industry, (R)-3-methylpiperidine is of particular interest due to its potential applications in the synthesis of active pharmaceutical ingredients (APIs). It is used as an intermediate in the production of drugs that require a piperidine ring structure for biological activity. The chiral nature of (R)-3-methylpiperidine allows for the selective targeting of specific receptors or enzymes, which is important for the development of drugs with improved efficacy and reduced side effects.

One notable application of (R)-3-methylpiperidine is in the synthesis of various alkaloid derivatives. Alkaloids are a diverse class of naturally occurring compounds with significant pharmacological effects, and many of these compounds contain piperidine rings as part of their molecular structure. The (R)-enantiomer of 3-methylpiperidine is particularly useful in the synthesis of compounds that mimic or modulate the action of neurotransmitters like acetylcholine, dopamine, and serotonin, which play key roles in the nervous system.

Additionally, (R)-3-methylpiperidine has been explored as a chiral building block in asymmetric synthesis. Its ability to induce chirality in the products of reactions makes it valuable in the synthesis of other complex molecules with high stereochemical purity. This property is particularly important in the production of drugs that require a specific stereochemistry to interact effectively with biological targets.

The compound's application extends beyond pharmaceuticals, as it is also used in the production of agrochemicals and other specialty chemicals. Its ability to undergo a variety of chemical transformations, including alkylation, acylation, and hydrogenation, makes it a versatile intermediate in the synthesis of other valuable chemical products.

In summary, (R)-3-methylpiperidine is a valuable compound with significant applications in the pharmaceutical and chemical industries. Its chiral nature enables its use in the synthesis of stereochemically specific compounds, particularly in the production of drugs and agrochemicals. The selective synthesis of (R)-3-methylpiperidine and its derivatives continues to be an area of active research, as the demand for chiral molecules in drug development and chemical synthesis grows.

References

1981. Differential electrophysiological and behavioral responses to optically active derivatives of phencyclidine. Naunyn-Schmiedeberg's Archives of Pharmacology, 316(1).
DOI: 10.1007/bf00499836