1-N-Boc-4-(Phenylamino)piperidine
[CAS# 125541-22-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 1-N-Boc-4-(Phenylamino)piperidine
• Synonyms: tert-butyl 4-anilinopiperidine-1-carboxylate
• Molecular Formula: C₁₆H₂₄N₂O₂
• Molecular Weight: 276.37
• CAS Registry Number: 125541-22-2
• EC Number: 864-150-6
• SMILES: CC(C)(C)OC(=O)N1CCC(CC1)NC2=CC=CC=C2

Properties

• Solubility: 9.449 mg/L (25 ºC water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.560, Calc.^*
• Melting point: 121.40 ºC
• Boiling Point: 400.6±38.0 ºC (760 mmHg), Calc.^*, 357.53 ºC
• Flash Point: 196.1±26.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

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

Hazard Classification

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

Discovory and Applicatios

1-N-Boc-4-(Phenylamino)piperidine, also known as Boc-4-AP, is a chemical compound first synthesized in the late 20th century by researchers exploring the synthesis of novel piperidine derivatives. The discovery of Boc-4-AP stemmed from efforts to develop compounds with potential applications in medicinal chemistry, particularly as intermediates or building blocks for the synthesis of pharmaceutical compounds. Its synthesis involves the protection of the amine group with a Boc (tert-butoxycarbonyl) protecting group, followed by the introduction of a phenylamino moiety onto the piperidine ring.

1-N-Boc-4-(Phenylamino)piperidine serves as a valuable intermediate in the synthesis of pharmaceutical compounds, particularly those targeting the central nervous system (CNS). Its piperidine ring structure and functional groups make it suitable for the introduction of various substituents and modifications, allowing for the synthesis of diverse pharmacologically active molecules.

In medicinal chemistry, Boc-4-AP is utilized in the design and synthesis of drugs targeting neurological disorders, psychiatric conditions, and pain management. Researchers modify Boc-4-AP to optimize its pharmacological properties, such as receptor affinity, metabolic stability, and blood-brain barrier penetration. By incorporating Boc-4-AP-derived motifs into drug candidates, medicinal chemists can explore new avenues for drug discovery and development.

Boc-4-AP is employed as a tool in neuroscience research to investigate the structure-activity relationships of neurotransmitter receptors and ion channels. Its piperidine scaffold and phenylamino group allow researchers to probe receptor-ligand interactions and study the effects of chemical modifications on receptor function and neuronal signaling. Boc-4-AP derivatives serve as pharmacological probes for studying neuronal excitability, synaptic transmission, and ion channel modulation.

Beyond its applications in medicinal chemistry and neuroscience, Boc-4-AP finds utility in organic synthesis as a versatile building block for the construction of complex molecules. Its ease of functionalization and compatibility with various synthetic methodologies make it a valuable tool for the synthesis of natural products, heterocyclic compounds, and other biologically relevant molecules.

Boc-4-AP is utilized in peptide synthesis as a protecting group for the amino group of amino acids. The Boc protecting group is commonly employed in solid-phase peptide synthesis to temporarily block the amino group, allowing for selective peptide bond formation and subsequent deprotection to reveal the free amine. Boc-4-AP's compatibility with peptide synthesis protocols and ease of removal make it a preferred protecting group strategy in the production of peptides for pharmaceutical, biochemical, and biotechnological applications.

References

2014. Synthesis of Chemokine Receptor Antagonist NIBR-1282. Synfacts.
DOI: 10.1055/s-0033-1340881

2019. Electrophilic Amination: An Update. Synlett.
DOI: 10.1055/s-0037-1611861

2022. Recent Advances to Mediate Reductive Processes of Nitroarenes Using Single-Electron Transfer, Organomagnesium, or Organozinc Reagents. Synthesis.
DOI: 10.1055/a-1792-6579