1-Boc-4-cyanopiperidine
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Product Description
1-Boc-4-cyanopiperidine, also known as tert-butyl 4-cyanopiperidine-1-carboxylate, is a Boc-protected piperidine derivative. It is widely used as an intermediate in pharmaceutical and fine chemical synthesis. 1-Boc-4-cyanopiperidine serves as a versatile and indispensable scaffold in synthetic chemistry, particularly in the pharmaceutical industry. Its combination of a protected amine and a transformable nitrile group makes it an ideal starting material for constructing a diverse array of piperidine-based compounds. It is commonly employed in peptide synthesis and medicinal chemistry, making it a valuable component in the development of new drugs and advanced materials.
Related Compounds
Related Compounds:
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4-Piperidinecarbonitrile: Deprotected form.
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1-Boc-4-(aminomethyl)piperidine: Nitrile-reduced form.
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1-Boc-4-piperidinecarboxylic acid: Nitrile-hydrolyzed form.
Synthesis Methods
Synthesis:
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Starting Materials: 4-Cyanopiperidine and Boc₂O (di-tert-butyl dicarbonate).
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Procedure: Typically synthesized by reacting 4-cyanopiperidine with Boc₂O in the presence of a base like Et₃N (triethylamine) or NaHCO₃ (sodium bicarbonate).
Uses and Applications
Applications:
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Medicinal Chemistry and Drug Discovery: Used as a building block in the synthesis of piperidine-containing pharmaceuticals, such as CNS-active compounds, kinase inhibitors, GPCR ligands, and neurotransmitter reuptake inhibitors.
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Pharmaceutical Intermediates: Commonly used in the synthesis of drugs due to the prevalence of the piperidine scaffold in bioactive molecules.
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Diversity-Oriented Synthesis: The dual functionality (Boc protection and cyano group) allows for late-stage diversification.
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Click Chemistry: The nitrile group can be converted to tetrazoles for 1,2,3-triazole formation.
Common Transformations:
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Boc Deprotection: Typically with TFA (trifluoroacetic acid) in DCM to yield 4-cyanopiperidine.
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Reduction of –CN Group: Can yield aminomethyl derivatives.
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Hydrolysis of –CN Group: Produces amide or carboxylic acid analogs depending on reaction conditions.
Properties and Characteristics
Chemical Information:
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IUPAC Name: tert-Butyl 4-cyanopiperidine-1-carboxylate
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Synonyms: 1-Boc-4-cyanopiperidine, N-Boc-4-cyanopiperidine, Tert-butyl 4-cyano-1-piperidinecarboxylate
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Molecular Formula: C₁₁H₁₈N₂O₂
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Molecular Weight: 210.27 g/mol
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Structure Summary: A piperidine ring with a cyano (-CN) group at the 4-position and a Boc (tert-butoxycarbonyl) protecting group on the nitrogen at position 1.
Physical and Chemical Properties:
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Appearance: White to off-white crystalline solid
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Melting Point: ~55-59 °C
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Boiling Point: ~305 °C (estimated)
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Density: ~1.1 g/cm³
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Solubility: Soluble in organic solvents like dichloromethane (DCM), ethyl acetate, methanol, chloroform, dimethylformamide (DMF), and acetone. Low solubility in water.
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Stability: Stable under normal conditions. The Boc group is cleavable under acidic conditions (e.g., with TFA).
Safety and Handling
Storage:
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Store under an inert atmosphere (N₂) at 0–4°C to prevent Boc migration or nitrile hydrolysis.
Hazards:
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The nitrile group is toxic and can release HCN under strong acid/base conditions. Handle in a fume hood with appropriate PPE (personal protective equipment).
Purification:
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Can be purified by flash chromatography (silica gel, EtOAc/hexanes) or distillation under reduced pressure.