657-36-3 | 4-(Trifluoromethyl)piperidine

CAS:657-36-3 | 4-(Trifluoromethyl)piperidine ,Description

4-(Trifluoromethyl)piperidine (4-TFP) is an organic compound with the molecular formula C5H9F3N. It is a colorless liquid with a pungent odor, and is a derivative of piperidine, a cyclic amine with a five-membered ring. 4-TFP is a versatile compound used in a variety of synthetic applications in organic chemistry. It is also a useful building block in the synthesis of pharmaceuticals and other organic compounds.
 

Scientific Research Applications

Synthesis of Piperidine Alkaloids4-(Trifluoromethyl)piperidine has been utilized in the synthesis of trifluoro-substituted analogues of mono-, di-, and trisubstituted piperidine alkaloids. These are achieved through diastereoselective synthesis from keto-protected 4-piperidones, prepared by an intramolecular Mannich-type reaction methodology. This process leads to the creation of new 2-(trifluoromethyl)-4-piperidinols and 4-amino

Scientific Research Applications of 4-(Trifluoromethyl)piperidine

Synthesis of Piperidine Alkaloids

4-(Trifluoromethyl)piperidine has been utilized in the synthesis of trifluoro-substituted analogues of mono-, di-, and trisubstituted piperidine alkaloids. These are achieved through diastereoselective synthesis from keto-protected 4-piperidones, prepared by an intramolecular Mannich-type reaction methodology. This process leads to the creation of new 2-(trifluoromethyl)-4-piperidinols and 4-amino-2-(trifluoromethyl)piperidines (Bariau et al., 2006) .

Molecular Structure Analysis

The crystal and molecular structure of 4-carboxypiperidinium chloride, a derivative of 4-(Trifluoromethyl)piperidine, has been characterized through X-ray diffraction, calculations, and FTIR spectrum analysis. This research provides insights into the conformation and interactions of such compounds, enhancing understanding of their structural properties (Szafran et al., 2007).

Synthetic Approach for Medicinal Chemistry

A study developed a convenient synthetic approach for preparing multigram amounts of 4-(trifluoromethoxy)piperidine and 4-(trifluoromethoxymethyl)piperidine, highlighting their potential as building blocks in medicinal chemistry. This approach includes acylation, transformation, desulfurization/fluorination, and other steps, demonstrating the versatility of 4-(Trifluoromethyl)piperidine derivatives (Logvinenko et al., 2021) .

Cationic Cyclisations in Chemical Synthesis

Trifluoromethanesulfonic acid, used in the synthesis of 4-(Trifluoromethyl)piperidine, acts as a catalyst in cyclisation processes to create pyrrolidines and homopiperidines. This study contributes to understanding the role of 4-(Trifluoromethyl)piperidine in facilitating efficient formation of polycyclic systems, a critical aspect in organic synthesis (Haskins & Knight, 2002).

Functionalization and Synthesis of Spiroox

Scientific Research Applications of 4-(Trifluoromethyl)piperidine

Synthesis of Piperidine Alkaloids

4-(Trifluoromethyl)piperidine is used in synthesizing trifluoro-substituted analogues of piperidine alkaloids. This process involves a diastereoselective synthesis from keto-protected 4-piperidones, leading to new 2-(trifluoromethyl)-4-piperidinols and 4-amino-2-(trifluoromethyl)piperidines. Such synthesis is valuable for developing bioactive compounds with enhanced properties (Bariau et al., 2006) .

Molecular Structure Analysis

The crystal and molecular structure of 4-carboxypiperidinium chloride, related to 4-(Trifluoromethyl)piperidine, has been studied using X-ray diffraction and computational methods. This research helps in understanding the structural properties of such compounds, which is crucial for their application in various scientific fields (Szafran et al., 2007).

Synthetic Approach for Medicinal Chemistry

A study focused on developing a synthetic approach for 4-(trifluoromethoxy)piperidine and its derivatives, highlighting their potential as building blocks in medicinal chemistry. This includes steps like acylation, transformation, and desulfurization/fluorination, showcasing the compound's versatility in synthesizing secondary amines with the CF3O-group (Logvinenko et al., 2021) .

Cationic Cyclisations in Chemical Synthesis

Trifluoromethanesulfonic acid, related to 4-(Trifluoromethyl)piperidine, is used as a catalyst for cyclisation processes in chemical synthesis. This is significant for the formation of complex polycyclic systems, such as pyrrolidines and homopiperidines, demonstrating the compound's role in efficient organic synthesis (Haskins & Knight, 2002).

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