Loratadine ketone
Overview
Description
Loratadine ketone is a complex organic compound with a unique structure that combines a piperidine ring, a pyridine ring, and a chlorophenyl group
Scientific Research Applications
Loratadine ketone has a wide range of scientific research applications, including:
Chemistry: It is used as a building block for the synthesis of more complex molecules and as a reagent in various organic reactions.
Biology: The compound is studied for its potential biological activities, including its interactions with enzymes and receptors.
Medicine: Research is ongoing to explore its potential therapeutic applications, such as its effects on neurological pathways and its use as a drug candidate.
Industry: The compound is used in the development of new materials and as an intermediate in the production of pharmaceuticals and agrochemicals.
Safety and Hazards
Mechanism of Action
Target of Action
It is known that many bioactive aromatic compounds containing similar structures have been found to bind with high affinity to multiple receptors .
Mode of Action
Compounds with similar structures have been found to interact with their targets, leading to various biological activities such as antiviral, anti-inflammatory, anticancer, anti-hiv, antioxidant, antimicrobial, antitubercular, antidiabetic, antimalarial, and anticholinesterase activities .
Biochemical Pathways
Compounds with similar structures have been found to affect a variety of biochemical pathways, leading to a broad spectrum of biological activities .
Result of Action
Compounds with similar structures have been found to have diverse biological activities and therapeutic possibilities .
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of Loratadine ketone typically involves multiple steps, including the formation of the piperidine ring, the introduction of the pyridine ring, and the attachment of the chlorophenyl group. Common synthetic routes may involve the use of reagents such as piperidine, pyridine, and chlorobenzene derivatives under specific reaction conditions, including controlled temperatures and the presence of catalysts.
Industrial Production Methods
Industrial production of this compound may involve large-scale chemical processes that ensure high yield and purity. Techniques such as continuous flow synthesis and the use of automated reactors can be employed to optimize the production process. The choice of solvents, catalysts, and purification methods is crucial to achieving the desired quality of the final product.
Chemical Reactions Analysis
Types of Reactions
Loratadine ketone can undergo various types of chemical reactions, including:
Oxidation: This reaction involves the addition of oxygen or the removal of hydrogen, often using oxidizing agents like potassium permanganate or hydrogen peroxide.
Reduction: This reaction involves the addition of hydrogen or the removal of oxygen, typically using reducing agents such as lithium aluminum hydride or sodium borohydride.
Substitution: This reaction involves the replacement of one functional group with another, often using reagents like halogens or alkylating agents.
Common Reagents and Conditions
The reactions of this compound often require specific reagents and conditions to proceed efficiently. For example, oxidation reactions may require acidic or basic conditions, while reduction reactions may need anhydrous solvents and inert atmospheres. Substitution reactions may be facilitated by the presence of catalysts or specific temperature and pressure conditions.
Major Products Formed
The major products formed from these reactions depend on the specific reagents and conditions used. For example, oxidation may yield ketones or carboxylic acids, reduction may produce alcohols or amines, and substitution may result in the formation of new functionalized derivatives.
Comparison with Similar Compounds
Similar Compounds
4,4’-Difluorobenzophenone: This compound has a similar structure with a benzophenone core and fluorine substituents.
Noble Gas Compounds: These compounds, although chemically distinct, share some similarities in terms of their reactivity and applications.
Uniqueness
Loratadine ketone is unique due to its specific combination of functional groups and its potential for diverse applications. Its structure allows for a wide range of chemical modifications, making it a versatile compound in scientific research.
Properties
IUPAC Name |
[3-[2-(3-chlorophenyl)ethyl]pyridin-2-yl]-(1-methylpiperidin-4-yl)methanone |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C20H23ClN2O/c1-23-12-9-17(10-13-23)20(24)19-16(5-3-11-22-19)8-7-15-4-2-6-18(21)14-15/h2-6,11,14,17H,7-10,12-13H2,1H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
YBWTYYOASANXND-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN1CCC(CC1)C(=O)C2=C(C=CC=N2)CCC3=CC(=CC=C3)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H23ClN2O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
342.9 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Q1: What is the significance of (1-Methyl-4-piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2-pyridinyl]methanone in the synthesis of Loratadine?
A1: This compound serves as a crucial precursor in the multi-step synthesis of Loratadine [, ]. Specifically, it undergoes further reactions, including hydrolysis, to ultimately yield Loratadine. This synthetic route, utilizing novel oxazoline intermediates, offers a potentially advantageous pathway for Loratadine production.
Q2: Can you elaborate on the specific reaction involving (1-Methyl-4-piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2-pyridinyl]methanone in the synthesis of Loratadine as described in the research?
A2: The research outlines a process where [2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-3-methyl-pyridine is reacted with 3-chlorobenzyl chloride, and subsequently treated with a Grignard reagent of 4-chloro-N-methyl-piperidine. This sequence ultimately yields (1-Methyl-4-piperidinyl)[3-[2-(3-chlorophenyl)ethyl]-2-pyridinyl]methanone] [, ]. This compound then undergoes hydrolysis as a critical step towards obtaining the final product, Loratadine.
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![1-Tert-butyl-3-[2-(3-methoxyphenoxy)-5-nitrophenyl]sulfonylurea](/img/structure/B110716.png)
