2-Benzyl-2,7-Diazaspiro[4.4]nonane-1,3-Dione HCl: Properties & Uses
2-Benzyl-2,7-Diazaspiro[4.4]nonane-1,3-Dione HCl: Properties & Uses
2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride is a spirocyclic imide building block featuring a unique bicyclic nitrogen-containing framework that makes it a valuable intermediate in medicinal chemistry and heterocyclic synthesis.
- Chemical Name
- 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride
- SKU
- B175431
- Core Scaffold
- Diazaspiro[4.4]nonane (spirocyclic imide with pyrrolidine ring)
- Functional Groups
- Imide (cyclic), benzyl N-substituent, secondary amine (as HCl salt)
- Salt Form
- Hydrochloride (HCl salt), enhances aqueous solubility and stability
- Primary Application
- Synthetic building block for drug discovery and heterocyclic compound libraries
Chemical Structure and Structural Features
2-Benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride belongs to the class of diazaspiro compounds, characterized by two fused rings sharing a single quaternary spiro carbon atom. The spiro[4.4]nonane backbone consists of two five-membered rings connected at the spiro center, incorporating two nitrogen atoms at positions 2 and 7 of the ring system.
The 1,3-dione motif in the first ring forms a cyclic imide (succinimide-type) functionality, while the nitrogen at position 7 resides in a pyrrolidine-type ring. The benzyl group attached to the imide nitrogen (position 2) provides a convenient protecting or directing group that can be removed under standard hydrogenolysis conditions, making this compound particularly versatile in multi-step synthesis.
The hydrochloride salt form protonates the secondary amine nitrogen at position 7, improving the compound's physicochemical properties—specifically its aqueous solubility and crystalline stability—which are desirable attributes for reagent-grade research materials.
Synthesis Relevance and Applications in Medicinal Chemistry
Spirocyclic scaffolds have gained considerable attention in modern drug discovery because they introduce three-dimensional complexity into small molecules, helping to improve selectivity and reduce off-target effects compared with planar aromatic systems. The diazaspiro[4.4]nonane core present in this compound is representative of a privileged spirocyclic framework encountered in bioactive natural products and pharmaceutical candidates.
2-Benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride (SKU: B175431) serves primarily as a synthetic building block for:
- Construction of focused compound libraries targeting central nervous system (CNS) receptors, where spirocyclic amines are well-represented among known pharmacophores.
- Fragment-based drug discovery campaigns requiring rigid, three-dimensionally defined scaffolds with orthogonal functional handles (imide and amine).
- Synthesis of spirocyclic analogues via N-alkylation, acylation, or reductive amination at the free amine (position 7) after salt neutralization.
- Preparation of more complex heterocyclic systems by ring-opening or ring-expansion chemistry leveraging the activated imide carbonyl groups.
The presence of both an imide and a protonated amine in the same molecule provides two distinct reactive sites, enabling divergent synthetic strategies from a single intermediate.
Handling, Storage, and Safety Considerations
As with all fine-chemical research reagents, proper handling and storage of 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride is essential to maintain purity and ensure researcher safety.
Storage: The compound should be stored in a tightly sealed container under cool, dry conditions, away from light and moisture. Standard laboratory storage at room temperature or under refrigeration (2–8 °C) is generally appropriate for hydrochloride salts of this type; researchers should consult the Certificate of Analysis (CoA) provided with each lot for specific recommended conditions.
Handling: Standard laboratory personal protective equipment (PPE) should be worn when handling this compound, including gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be conducted in a well-ventilated area or fume hood.
Disposal: Disposal must comply with applicable local, regional, and national regulations governing chemical waste. Researchers should consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for detailed hazard classifications, first-aid measures, and disposal guidance specific to this product.
Quality and Availability from Aladdin Scientific
Aladdin Scientific offers 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride (SKU: B175431) as a catalog reagent suitable for research and development applications. Each lot is accompanied by a Certificate of Analysis detailing purity, appearance, and analytical data to support reproducible experimental outcomes.
Researchers requiring this compound for drug discovery, combinatorial chemistry, or heterocyclic synthesis programs can order directly through the Aladdin Scientific website. Custom quantities or bulk orders may be available; contact Aladdin Scientific's technical sales team for further information on availability, pricing, and lead times.
For questions regarding the suitability of this reagent for specific applications, spectral data, or additional characterization information, Aladdin Scientific's technical support team is available to assist.
Frequently asked questions
What is 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride used for?
This compound is used primarily as a synthetic building block in medicinal chemistry and drug discovery. Its spirocyclic diazanonane core provides three-dimensional structural complexity, and the orthogonal imide and amine functional groups allow diverse chemical transformations for the preparation of complex heterocyclic compounds and focused compound libraries.
Why is this compound supplied as a hydrochloride salt?
The hydrochloride salt form is produced by protonating the secondary amine nitrogen in the pyrrolidine ring. This salt form typically offers improved aqueous solubility, greater crystalline stability, and easier handling compared with the free base, making it preferable for storage and distribution as a research reagent.
Can the benzyl group on the imide nitrogen be removed?
Yes, the benzyl group on the imide nitrogen is typically removable by catalytic hydrogenolysis (e.g., Pd/C under hydrogen atmosphere), which is a standard method for N-debenzylation in synthetic chemistry. This allows the compound to serve as a protected-amine precursor, with the free NH imide accessible after deprotection for further functionalization.
How should I store this reagent to maintain its purity?
The compound should be stored in a tightly sealed container, protected from moisture, light, and heat. Consult the Certificate of Analysis (CoA) provided with your specific lot for Aladdin Scientific's recommended storage temperature and conditions. Proper sealing after each use is advised to prevent moisture absorption, which can be a concern for hydrochloride salts.
Where can I order 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride?
This compound is available from Aladdin Scientific under SKU B175431 and can be ordered directly through the Aladdin Scientific website. For bulk quantities or customized requirements, please contact the Aladdin Scientific sales team for pricing, availability, and lead time information.
References
- Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. doi:10.1021/jm901241e
- Stepan, A. F. et al. Application of the Bicyclo[1.1.1]pentane Motif as a Nonclassical Phenyl Bioisostere in the Design of a Potent and Orally Active γ-Secretase Inhibitor. J. Med. Chem. 2012, 55, 3414–3424. [Cited as representative spirocycle drug-discovery reference; verify applicability to diazaspiro scaffold.]
- Aladdin Scientific. Product Listing: 2-benzyl-2,7-diazaspiro[4.4]nonane-1,3-dione hydrochloride, SKU B175431. Certificate of Analysis available upon request.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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