Introduction
1-Boc Piperazine (1-tert-Butoxycarbonylpiperazine) is a widely used chemical intermediate in organic synthesis, particularly within the pharmaceutical and biotech industries. With a protected piperazine core, it serves as a versatile compound in the development of drug candidates, bioactive molecules, and custom chemical scaffolds. The Boc (tert-butoxycarbonyl) protecting group offers selective reactivity and stability, making 1-Boc Piperazine ideal for multi-step synthesis.
Chemical Overview
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Chemical Name: 1-(tert-Butoxycarbonyl)piperazine
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Molecular Formula: C9H18N2O2
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Molecular Weight: 186.25 g/mol
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CAS Number: 57260-71-6
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Structure: Piperazine ring with one nitrogen substituted by a Boc group
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Appearance: White to off-white crystalline solid
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Solubility: Soluble in methanol, ethanol, dichloromethane, and most polar organic solvents
The piperazine moiety is common in many drugs due to its favorable pharmacokinetic and receptor-binding properties, while the Boc group offers controlled protection for selective reactions.
Applications of 1-Boc Piperazine
1. Pharmaceutical Intermediate
1-Boc Piperazine plays a critical role in the synthesis of active pharmaceutical ingredients (APIs). It is frequently used in the preparation of:
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Antipsychotic drugs
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Antidepressants
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Anti-inflammatory agents
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Anticancer molecules
By protecting one of the nitrogen atoms on the piperazine ring, it allows for controlled modification of the other, which is essential in stepwise drug synthesis.
2. Medicinal Chemistry & Lead Optimization
In drug discovery and medicinal chemistry, 1-Boc Piperazine is commonly incorporated into combinatorial libraries for screening biological activity. The piperazine scaffold is highly valued for:
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Enhancing water solubility
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Improving membrane permeability
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Acting as a bioisostere for amines or peptides
The Boc group can be easily removed using acid (e.g., TFA), providing flexibility in late-stage functionalization.
3. Peptidomimetic Design
Piperazine-based compounds like 1-Boc Piperazine are often used in the design of peptidomimetics. These are compounds that mimic peptide structures but are more stable and resistant to enzymatic degradation. 1-Boc Piperazine helps in creating:
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Enzyme inhibitors
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Receptor antagonists
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Molecular probes
This application is particularly important in the development of drugs targeting GPCRs, kinases, and enzymatic pathways.
Safety and Handling
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Hazard Classification: Low; may cause irritation upon direct contact
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Handling Precautions: Use appropriate PPE (gloves, goggles); handle in a fume hood if large volumes are used
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Storage Conditions: Store in a tightly sealed container, away from strong acids and heat sources; recommended storage temperature: below 25°C
Packaging and Availability
1-Boc Piperazine is available in:
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Lab Packs: 5g, 25g, 100g
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Bulk Quantities: 500g, 1kg, 5kg, and customized packaging on request
All batches come with COA, MSDS, and batch-specific documentation. Shipping is available worldwide.
Conclusion
1-Boc Piperazine is a strategically important intermediate in modern chemical synthesis, especially for pharmaceutical applications. Its combination of a reactive piperazine ring and a removable Boc group makes it a go-to building block for chemists involved in drug discovery, peptide chemistry, and heterocycle design. Its ease of use, stability, and broad reactivity spectrum continue to make it a valuable compound in both research and commercial manufacturing.
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3. Custom Peptidomimetic Synthesis
In the design of peptidomimetics, 1-Boc Piperazine serves as a flexible spacer or scaffold that mimics peptide bonds, useful in:
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Enzyme inhibitors
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Signal transduction mimics
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Receptor ligands
Handling and Safety
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Hazards: May cause skin or eye irritation
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Precautions: Handle with gloves and eye protection; avoid inhalation or prolonged exposure
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Storage Conditions: Store in a tightly sealed container, in a cool, dry place away from acids
Packaging and Supply
Available in:
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Small Packs: 5g, 25g, 100g for research use
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Bulk Quantities: 1kg, 5kg, and custom volumes for commercial production
Supplied with COA, MSDS, and global shipping options.
Conclusion
1-Boc Piperazine is a cornerstone intermediate in the field of organic and medicinal chemistry. Its versatility, ease of use, and clean deprotection make it a preferred choice for researchers and manufacturers developing advanced drug candidates and custom molecules.
Need bulk or custom-packed 1-Boc Piperazine? Contact us for quotations, technical documentation, and application support tailored to your R&D or production goals.
Structural Features
1-Boc Piperazine consists of a six-membered piperazine ring, where one nitrogen is protected with a tert-butoxycarbonyl (Boc) group. This protection:
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Enhances the selective functionalization of the second nitrogen
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Provides stability under basic conditions
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Is easily removed under acidic conditions, making it ideal for stepwise synthesis
Applications of 1-Boc Piperazine
1. Pharmaceutical Intermediate
It is a key building block in the synthesis of several classes of drugs, including:
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Antipsychotics
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Antidepressants
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Anti-inflammatory agents
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Anti-cancer compounds
The Boc group allows for temporary protection during multi-step synthesis, enabling the development of diverse heterocyclic scaffolds.
2. Medicinal Chemistry and Drug Discovery
1-Boc Piperazine is commonly used in combinatorial chemistry and lead optimization, offering:
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Increased lipophilicity
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Improved pharmacokinetic properties
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Potential for receptor binding enhancement
Synthesis of 1-Boc Piperazine
1-Boc Piperazine is synthesized by reacting piperazine with di-tert-butyl dicarbonate (Boc₂O) under basic conditions (commonly with triethylamine or sodium bicarbonate). This selective reaction introduces the Boc group to one nitrogen atom, leaving the other available for further modification. The Boc group is acid-labile, meaning it can be easily removed with trifluoroacetic acid (TFA) or HCl in dioxane — a common step in deprotection strategies.
Pharmaceutical and Industrial Applications
1. Intermediate for Drug Molecules
Piperazine-based compounds appear in over 20 approved drugs, such as:
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Ciprofloxacin (antibiotic)
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Risperidone (antipsychotic)
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Sildenafil (vasodilator)
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Dasatinib (anticancer)
1-Boc Piperazine serves as a protected precursor, simplifying the synthetic route to such molecules by providing clean, reproducible, and controlled substitution.
2. Lead Optimization & Structure-Activity Relationship (SAR) Studies
Due to its solubility and flexibility, medicinal chemists use 1-Boc Piperazine during lead generation and SAR exploration. It contributes to better:
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Receptor binding affinity
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Lipophilicity tuning
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Solubility improvements
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Metabolic stability
3. Scaffold in Peptidomimetics and Macrocycles
1-Boc Piperazine is widely used in macrocyclic drugs and peptidomimetic design, where its nitrogen atoms and ring flexibility help mimic natural peptides. These features are essential for creating protease inhibitors, antiviral agents, and enzyme blockers.