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1-Boc Piperazine: A Critical Intermediate in Medic
1-Boc Piperazine: A Critical Intermediate in Medic
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lifechampharma56
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Jul 27, 2025
9:40 PM
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Overview
1-Boc Piperazine
(tert-Butyl 4-piperazinecarboxylate) is an essential protected derivative of piperazine, commonly used in pharmaceutical R&D, combinatorial chemistry, and intermediate synthesis. Its primary value lies in its selectively protected nitrogen atom, which makes it an ideal substrate for further functionalization without affecting the entire piperazine ring.
Chemical and Physical Properties
Chemical Name: 1-(tert-Butoxycarbonyl)piperazine
Synonyms: Boc-piperazine, tert-butyl piperazine-1-carboxylate
Molecular Formula: C9H18N2O2
Molecular Weight: 186.25 g/mol
CAS Number: 57260-71-6
Appearance: White to pale yellow crystalline powder
Boiling Point: Approx. 335°C (decomposes)
Solubility: Freely soluble in common organic solvents like dichloromethane (DCM), acetonitrile, and methanol
Its structure contains a six-membered piperazine ring substituted with a Boc protecting group on one nitrogen. This feature ensures regioselective reactivity, ideal for stepwise synthesis in both industrial and academic labs.
Synthesis of 1-Boc Piperazine
1-Boc Piperazine is synthesized by reacting piperazine with di-tert-butyl dicarbonate (Boc?O) 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:
Ciprofloxacin (antibiotic)
Risperidone (antipsychotic)
Sildenafil (vasodilator)
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:
Receptor binding affinity
Lipophilicity tuning
Solubility improvements
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.
Advantages of Boc Protection
The Boc group offers:
Stability during base-sensitive reactions
Easy deprotection under mild acid
Increased synthetic selectivity
Minimized side reactions during multi-step synthesis
Its compatibility with automated synthesis platforms makes it indispensable for combinatorial chemistry libraries.
Storage and Handling
Shelf-life: Stable under normal conditions if kept dry and away from light
Storage Temperature: 2°C – 8°C recommended for extended shelf life
Hazards: May cause irritation; not considered highly toxic
Precautions: Use gloves, lab coat, and goggles; handle in well-ventilated area
Always refer to the Material Safety Data Sheet (MSDS) for proper handling guidelines.
Packaging and Availability
Offered by chemical suppliers in:
Research packs: 1g, 5g, 25g, 100g
Bulk & commercial lots: 1kg, 5kg, 25kg, with custom contract manufacturing available
Documentation: Supplied with COA, MSDS, TDS, and batch analysis reports. Export supported globally with REACH & ISO compliance as required.
Conclusion
1-Boc Piperazine is an indispensable tool for organic and medicinal chemists. Its protected structure, ease of functionalization, and pharmacological relevance make it a go-to intermediate in the development of next-generation therapeutics. Whether you're working in drug discovery, process chemistry, or academic research, this versatile compound supports innovation with efficiency, flexibility, and reproducibility.
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