What Is 3-(4-(Piperidin-4-yl)phenyl)piperidine-2,6-dione Hydrochloride?

3-(4-(Piperidin-4-yl)phenyl)piperidine-2,6-dione hydrochloride (Aladdin SKU C1529524) is a synthetic small molecule comprising two pharmacophoric elements: a piperidine-2,6-dione (glutarimide) ring and a 4-substituted piperidine connected through a para-phenylene linker. The salt form (hydrochloride) is supplied to improve aqueous solubility and solid-state stability relative to the free base.

The glutarimide motif is the hallmark of thalidomide-class immunomodulatory drugs (IMiDs) and is responsible for binding to the substrate recognition domain of cereblon (CRBN), the substrate receptor component of the CRL4^CRBN E3 ubiquitin ligase complex. Because of this recognition element, the compound is widely employed as a cereblon-recruiting warhead or linker intermediate in the construction of Proteolysis-Targeting Chimeras (PROTACs) and molecular glue degraders intended for targeted protein degradation research.

Physical and Chemical Properties

The compound exists as a hydrochloride salt, which typically confers improved hygroscopicity management and crystalline stability compared with the free base. Key physicochemical considerations for researchers include:

• Appearance: Expected to be a white to off-white solid; verify certificate of analysis (CoA) for lot-specific data.
• Solubility: The hydrochloride salt generally exhibits improved solubility in water and DMSO relative to the free base. DMSO stock solutions are commonly prepared for biological assays.
• Stability: The glutarimide ring can be susceptible to hydrolysis under strongly basic conditions; avoid prolonged exposure to high pH aqueous environments.
• Molecular weight: The free base molecular formula C₁₆H₂₀N₂O₂ corresponds to a molecular weight of approximately 272.34 g/mol; the hydrochloride salt adds approximately 36.46 g/mol.

Note: Confirm all lot-specific values (purity, melting point, exact MW) against the provided CoA.

Storage and Handling Guidelines

Proper storage and handling preserve compound integrity and ensure reliable experimental results:

• Storage temperature: Store at 2–8 °C (refrigerator) or −20 °C (freezer) in a tightly sealed container away from light and moisture. Follow the conditions specified on the product label and CoA.
• Container: Keep in the original, tightly closed container under inert atmosphere (argon or nitrogen) if the product is moisture-sensitive.
• Stock solution preparation: Prepare DMSO stock solutions at ≤10 mM or as optimized for the assay; aliquot to avoid repeated freeze-thaw cycles, which can degrade sensitive compounds.
• Personal protective equipment (PPE): As with all research chemicals of unknown full toxicological profile, handle with appropriate PPE including gloves, lab coat, and eye protection. Consult the Safety Data Sheet (SDS) prior to use.
• Disposal: Dispose of waste in accordance with local regulations for organic nitrogen-containing compounds.

Research Applications and Context

This compound occupies an important niche in targeted protein degradation (TPD) research. Its dual-ring architecture provides both a cereblon-binding glutarimide and a secondary piperidine nitrogen that can be functionalized with linkers to attach a protein-of-interest (POI) ligand, enabling PROTAC assembly:

• PROTAC synthesis: The free piperidine NH (or its protected derivative) serves as a synthetic handle for attaching diverse linkers via amide bond formation, reductive amination, or other coupling strategies.
• Molecular glue research: Glutarimide-containing scaffolds inform the design of molecular glue degraders that redirect CRBN toward neo-substrates.
• Structure-activity relationship (SAR) studies: The compound can be used to explore how phenyl-linker geometry and piperidine substitution affect CRBN binding affinity and ternary complex formation.
• Chemical biology tool compound: Useful as a reference or control in assays measuring cereblon engagement.

Researchers should validate CRBN binding independently using biophysical or cell-based assays, as activity can be context- and construct-dependent.

Ordering, Specifications, and Quality

3-(4-(Piperidin-4-yl)phenyl)piperidine-2,6-dione hydrochloride is available from Aladdin Scientific under SKU C1529524. When ordering, researchers and procurement teams should consider the following:

• Purity: Request and review the Certificate of Analysis (CoA) for each lot. Typical research-grade purity targets are ≥95% by HPLC; confirm the specific purity specification on the product page before ordering.
• Available quantities: Contact Aladdin Scientific's sales team for available pack sizes and bulk pricing if larger quantities are required for library synthesis.
• Documentation: CoA, SDS, and NMR/HPLC spectra may be available upon request; inquire at time of ordering.
• Lead time: Lead time may vary by stock status; check the product page or contact customer service for real-time availability.
• Shipping: The compound should be shipped under conditions appropriate for its stability (cool/dry); confirm shipping requirements with Aladdin Scientific at the time of order.