N-Benzyl-4-piperidone
[CAS# 3612-20-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: N-Benzyl-4-piperidone
• Synonyms: 1-(Phenylmethyl)-4-piperidinone; 1-Benzylpiperidin-4-one
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.26
• CAS Registry Number: 3612-20-2
• EC Number: 222-782-4
• SMILES: C1CN(CCC1=O)CC2=CC=CC=C2

Properties

• Density: 1.069
• Boiling point: 114-116 °C (0.4 mmHg)
• Refractive index: 1.539-1.54
• Flash point: 71 °C
• Water solubility: 12 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

N-Benzyl-4-piperidone is a synthetic organic compound belonging to the class of piperidones. Its discovery is rooted in the extensive research on piperidine derivatives, which have been studied for their diverse pharmacological properties. The synthesis of N-Benzyl-4-piperidone typically involves the benzylation of 4-piperidone, a reaction that introduces a benzyl group to the nitrogen atom of the piperidone ring. This compound has garnered attention due to its unique structural properties, which facilitate its use as an intermediate in the synthesis of various pharmaceuticals and organic compounds. The precise date and context of its initial synthesis are not well-documented, but its emergence is closely tied to the mid-20th century boom in organic and medicinal chemistry research.

N-Benzyl-4-piperidone is extensively used as an intermediate in the synthesis of a wide range of pharmaceutical compounds. Its structure serves as a versatile scaffold for creating complex molecules, particularly in the development of drugs targeting the central nervous system. For instance, it plays a crucial role in the synthesis of certain analgesics, antipsychotics, and antidepressants. The benzyl group attached to the piperidone ring enhances the compound's ability to cross the blood-brain barrier, making it a valuable precursor in neuropharmacology.

In chemical research, N-Benzyl-4-piperidone is utilized as a building block for the synthesis of more complex molecules. Its reactive carbonyl group and the benzyl moiety allow for various chemical modifications, making it a useful reagent in organic synthesis. Researchers exploit these properties to explore new chemical reactions and pathways, thereby advancing the field of synthetic chemistry. Its applications extend to the development of new methodologies in the synthesis of heterocyclic compounds, which are prevalent in many natural products and pharmaceuticals.

Beyond pharmaceuticals, N-Benzyl-4-piperidone finds applications in the manufacture of agrochemicals and dyes. Its intermediacy is valuable in producing compounds that protect crops from pests and diseases, contributing to agricultural productivity. Additionally, the compound is used in the synthesis of certain dyes and pigments, where its chemical stability and reactivity are advantageous.

Given its structural characteristics, N-Benzyl-4-piperidone is also explored in drug discovery programs. Its ability to act as a precursor to various bioactive compounds makes it a candidate for the development of new therapeutic agents. Researchers are investigating its derivatives for potential anti-cancer, anti-inflammatory, and antiviral properties, hoping to uncover new treatments for a range of diseases.

References

2019. Piperidine Derivatives in Drug Discovery. European Journal of Medicinal Chemistry, 181.
DOI: 10.1016/j.ejmech.2019.111587