1-Cyclopentyl-4-aminopiperidine: Properties & Applications

1-Cyclopentyl-4-aminopiperidine is a bifunctional piperidine derivative bearing both a cyclopentyl N-substituent and a primary 4-amino group, making it a versatile building block for the synthesis of pharmacologically active compounds and drug candidates.

Chemical Name

1-Cyclopentyl-4-aminopiperidine

SKU / Catalog Number

C181184

Molecular Formula

C10H20N2

Molecular Weight

168.28 g/mol

Functional Groups

Secondary amine (piperidine N), primary amine (4-amino), cyclopentyl ring

Primary Use

Synthetic intermediate and building block in medicinal chemistry and drug discovery

Chemical Structure and Key Properties

1-Cyclopentyl-4-aminopiperidine (CAS catalog SKU: C181184) is a saturated heterocyclic compound with the molecular formula C₁₀H₂₀N₂ and a molecular weight of approximately 168.28 g/mol. Its structure consists of a six-membered piperidine ring in which the ring nitrogen bears a cyclopentyl substituent at the 1-position, and a primary amino group (-NH₂) is located at the 4-position of the ring.

The compound possesses two basic nitrogen centers: the tertiary piperidine nitrogen and the primary amine at the 4-position. This bifunctional character confers significant synthetic versatility, allowing the molecule to participate in a wide variety of chemical transformations including acylation, sulfonylation, reductive amination, and condensation reactions. The cyclopentyl group at the ring nitrogen provides enhanced lipophilicity relative to unsubstituted 4-aminopiperidine, which can favorably influence the pharmacokinetic profile of derived compounds.

As a saturated amine, 1-Cyclopentyl-4-aminopiperidine is expected to be a solid or low-melting solid at room temperature. Researchers should store this reagent under cool, dry, and inert-atmosphere conditions to prevent oxidation or moisture absorption, which are common concerns for primary amine-containing compounds.

Role as a Building Block in Medicinal Chemistry

Piperidine is one of the most prevalent heterocyclic scaffolds found in approved pharmaceuticals and drug candidates, and N-substituted 4-aminopiperidines represent an important subclass widely exploited in drug discovery programs. 1-Cyclopentyl-4-aminopiperidine extends this utility by incorporating a cycloalkyl group on the ring nitrogen, a structural motif associated with improved metabolic stability compared to linear alkyl or aryl substituents in some contexts.

The primary amine at the 4-position serves as the principal handle for derivatization. It can be readily reacted with carboxylic acids (via amide coupling), acid chlorides, sulfonyl chlorides (to form sulfonamides), isocyanates (to form ureas), aldehydes or ketones (via reductive amination), and activated heterocycles (via nucleophilic aromatic substitution). These transformations enable rapid generation of structurally diverse libraries for structure-activity relationship (SAR) studies.

Compounds derived from N-cycloalkyl-4-aminopiperidine scaffolds have appeared in the literature as kinase inhibitors, GPCR modulators, and central nervous system (CNS) drug candidates, reflecting the pharmacological relevance of this chemical space. 1-Cyclopentyl-4-aminopiperidine thus serves as a privileged starting material for researchers aiming to access bioactive chemical space efficiently.

Handling, Safety, and Storage Recommendations

As with all low-molecular-weight primary and tertiary amines, 1-Cyclopentyl-4-aminopiperidine should be handled with appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety glasses, and a laboratory coat. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to amine vapors.

Amine compounds can be corrosive to skin and mucous membranes and may be harmful if inhaled or ingested. Users should consult the Safety Data Sheet (SDS) provided with the product before use. In the event of skin or eye contact, the affected area should be flushed thoroughly with water and medical attention sought if irritation persists.

For storage, the compound should be kept in a tightly sealed container under an inert gas (nitrogen or argon) blanket, away from moisture, oxidizing agents, and strong acids. A cool, dry environment (e.g., 2–8 °C or room temperature as specified in product documentation) is recommended to maximize shelf life. Researchers should verify specific storage conditions from the product label and SDS supplied by Aladdin Scientific.

Ordering Information and Quality Specifications

1-Cyclopentyl-4-aminopiperidine is available from Aladdin Scientific under catalog number C181184. Aladdin Scientific supplies research-grade reagents with documented purity specifications; customers are encouraged to review the certificate of analysis (CoA) available for each lot to confirm identity (typically by NMR or GC-MS), purity (typically assessed by GC or HPLC), and physical characteristics prior to use in sensitive applications.

For bulk quantities, custom packaging, or special purity grades, research teams and procurement officers should contact Aladdin Scientific's customer support team directly to discuss requirements and obtain a quotation. Volume pricing may be available for larger orders, and the Aladdin rewards program may provide additional savings for qualifying institutions.

When placing an order, users should reference the SKU C181184 to ensure the correct product is selected. Up-to-date pricing, stock availability, and shipping options can be found on the Aladdin Scientific website or by contacting the sales team.

Frequently asked questions

What is 1-Cyclopentyl-4-aminopiperidine used for in research?

1-Cyclopentyl-4-aminopiperidine is primarily used as a synthetic building block in medicinal chemistry and drug discovery. Its bifunctional nature—combining a reactive primary amine at the 4-position with an N-cyclopentyl piperidine core—enables diverse chemical derivatizations, including amide coupling, reductive amination, urea formation, and sulfonamide synthesis, facilitating SAR library generation.

How should 1-Cyclopentyl-4-aminopiperidine be stored to ensure stability?

The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon), protected from moisture and oxidizing agents. A cool, dry environment is recommended. Users should refer to the specific storage conditions stated on the Aladdin Scientific product label and SDS for authoritative guidance.

What is the catalog number for 1-Cyclopentyl-4-aminopiperidine at Aladdin Scientific?

1-Cyclopentyl-4-aminopiperidine is listed under catalog number C181184 at Aladdin Scientific. Customers can use this SKU to locate the product on the Aladdin Scientific website or when communicating with the sales and customer service teams.

What types of chemical reactions can be performed using the primary amine group of this compound?

The primary amine at the 4-position of 1-Cyclopentyl-4-aminopiperidine can undergo acylation with carboxylic acids or acid chlorides to form amides, sulfonylation to form sulfonamides, reaction with isocyanates to yield ureas, reductive amination with aldehydes or ketones, and nucleophilic aromatic substitution on activated heterocycles. These reactions make it highly valuable for combinatorial and parallel synthesis campaigns.

References

1. Patani, G. A.; LaVoie, E. J. Bioisosterism: A Rational Approach in Drug Design. Chemical Reviews, 1996, 96(8), 3147–3176. doi:10.1021/cr950066q
2. Vitaku, E.; Smith, D. T.; Njardarson, J. T. Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals. Journal of Medicinal Chemistry, 2014, 57(24), 10257–10274. doi:10.1021/jm501100b
3. Aladdin Scientific Product Page: 1-Cyclopentyl-4-aminopiperidine, SKU C181184.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.