1-Cbz-4-Piperidone
[CAS# 19099-93-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 1-Cbz-4-Piperidone
• Synonyms: N-Benzyloxycarbonyl-4-piperidone; Benzyl 4-oxo-1-piperazinecarboxylate
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.26
• CAS Registry Number: 19099-93-5
• EC Number: 606-227-7
• SMILES: C1CN(CCC1=O)C(=O)OCC2=CC=CC=C2

Properties

• Density: 1.172
• Melting point: 38-41 °C
• Boiling point: 114-140 °C (0.25 mmHg)
• Refractive index: 1.542
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H412
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1-Cbz-4-piperidone, also known as N-carbobenzyloxy-4-piperidone, was first synthesized through organic chemistry techniques aimed at modifying the structure of piperidone derivatives. The synthesis process typically involves the protection of the nitrogen atom of piperidone with a carbobenzyloxy (Cbz) group, resulting in the formation of 1-Cbz-4-piperidone. This compound's discovery marked a significant advancement in organic synthesis.

1-Cbz-4-piperidone serves as a crucial intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the production of various drugs, including analgesics, antipsychotics, and antivirals. Chemical modifications of the piperidone or the Cbz group enable the creation of drug candidates with improved efficacy, bioavailability, or selectivity

In the agricultural sector, 1-Cbz-4-piperidone finds application as a precursor for the synthesis of agrochemicals and pesticides. Piperidone derivatives possess pesticidal properties, and modifications of their structure can enhance their effectiveness against pests and weeds. By incorporating 1-Cbz-4-piperidone into pesticide formulations, researchers aim to develop products that can protect crops from damage caused by insects, fungi, and other pathogens

1-Cbz-4-piperidone is valuable as an intermediate in organic synthesis, facilitating the production of various chemical compounds with diverse applications. Its incorporation into multistep synthesis pathways enables the creation of complex molecules used in pharmaceuticals, agrochemicals, and materials science.

Beyond its established applications, ongoing research explores new uses for 1-Cbz-4-piperidone in fields such as material science, catalysis, and drug discovery. Scientists investigate its reactivity, properties, and potential interactions with other molecules to develop innovative materials, catalysts, and chemical processes.

In laboratory settings, 1-Cbz-4-piperidone serves as a solvent or reagent in chemical reactions and synthesis processes. Its solubility properties and compatibility with a wide range of organic and inorganic compounds make it useful for dissolving or reacting with other substances to form desired products.

References

2019. Application of Organometallic Catalysts in API Synthesis. Organometallics in Process Chemistry, 3418.
DOI: 10.1007/3418_2019_31

2018. Recent Advances in the Applications of Triethylsilane in Organic Synthesis. Synthesis, 50(14).
DOI: 10.1055/s-0037-1610107

2013. Microwave-Assisted Synthesis. Science of Synthesis, 210.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-210-00325