(R)-3-Aminopiperidine dihydrochloride
[CAS# 334618-23-4]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (R)-3-Aminopiperidine dihydrochloride
• Synonyms: (R)-(-)-3-Aminopiperidine dihydrochloride; (R)-3-Piperidinamine dihydrochloride
• Molecular Formula: C₅H₁₄Cl₂N₂
• Molecular Weight: 173.08
• CAS Registry Number: 334618-23-4
• EC Number: 608-870-9
• SMILES: C1C[C@H](CNC1)N.Cl.Cl

Properties

• Melting point: 205-209 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

(R)-3-Aminopiperidine dihydrochloride is an essential chiral building block in medicinal chemistry and drug development. (R)-3-Aminopiperidine dihydrochloride was developed as part of an effort to find an efficient chiral intermediate for drug synthesis. The compound is the hydrochloride salt of (R)-3-aminopiperidine, a chiral amine with a piperidine ring that is frequently used due to its stability and ease of handling. The synthesis of (R)-3-aminopiperidine dihydrochloride typically involves asymmetric synthesis or resolution techniques to achieve the desired enantiomeric purity. A common approach is to reduce the chiral piperidone precursor, using a chiral catalyst or reagent to ensure the formation of the (R)-enantiomer. The resulting amine is then converted to its dihydrochloride salt to enhance its solubility and stability.

(R)-3-Aminopiperidine dihydrochloride is a crystalline solid that is extremely soluble in water. Its molecular formula is C5H14Cl2N2 and is characterized by the chiral center being located at the 3-position of the piperidine ring, which determines its (R)-configuration. This chirality is essential for its role as a chiral building block in asymmetric synthesis.

The main application of (R)-3-aminopiperidine dihydrochloride is as a chiral building block in the synthesis of various APIs. Due to its chirality, it can be used to build molecules with specific three-dimensional shapes, which is essential for the activity of many drugs. This application is particularly important in the development of drugs targeting diseases, as stereochemistry can affect the efficacy and safety of drugs.

The compound is integral to the synthesis of a variety of drugs, including antiviral, anticancer, and central nervous system (CNS) drugs. For example, it is used to synthesize piperidinyl inhibitors, which target specific enzymes or receptors involved in disease processes. The configuration of the (R)-enantiomer often helps provide the correct spatial orientation for interaction with the biological target, thereby helping to achieve the desired pharmacological activity.

(R)-3-aminopiperidine dihydrochloride is used in asymmetric synthesis, and its chirality helps to produce enantiomerically pure compounds. This is essential for the development of drugs with high specificity and reduced side effects. The compound can serve as a starting material for creating complex molecular structures in a stereocontrolled manner.

In addition to its use in drug synthesis, (R)-3-aminopiperidine dihydrochloride is also of great value in chemical research and development. It is used to explore new synthetic methods, develop new catalytic processes, and study the effects of chirality on chemical reactions and biological activities.

References

2012. Recent Developments on the Trifluoromethylation of (Hetero)Arenes. Chemistry - An Asian Journal, 7(7).
DOI: 10.1002/asia.201200211

2014. Synthesis of Fluorinated Pyridines. Fluorine in Heterocyclic Chemistry Volume 2.
DOI: 10.1007/978-3-319-04435-4_1

1988. Olfactory and hepatic changes following inhalation of 3-trifluoromethyl pyridine in rats. Toxicology, 50(1).
DOI: 10.1016/0300-483x(88)90121-7