(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride
Overview
Description
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride is a chemical compound with the molecular formula C12H15ClF2N2O and a molecular weight of 276.71 g/mol . This compound is known for its applications in the pharmaceutical industry, particularly as an intermediate in the synthesis of various drugs .
Mechanism of Action
Target of Action
It is known to be an intermediate in the synthesis of risperidone , which primarily targets dopamine D2 and serotonin 5-HT2 receptors in the brain.
Mode of Action
If it is indeed an intermediate in the synthesis of risperidone , it may contribute to the antipsychotic effects of the final product by interacting with dopamine and serotonin receptors.
Biochemical Pathways
As an intermediate in the synthesis of risperidone , it may indirectly influence the dopaminergic and serotonergic pathways in the brain.
Pharmacokinetics
As an intermediate in the synthesis of risperidone , its pharmacokinetic properties may be transformed during the synthesis process.
Result of Action
As an intermediate in the synthesis of risperidone , it may contribute to the antipsychotic effects of the final product.
Action Environment
It is recommended to store the compound under inert gas (nitrogen or argon) at 2-8°c .
Biochemical Analysis
Biochemical Properties
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride plays a significant role in various biochemical reactions. It interacts with several enzymes, proteins, and other biomolecules. For instance, it has been observed to interact with cytochrome P450 enzymes, which are crucial for the metabolism of many drugs . The nature of these interactions often involves the inhibition or modulation of enzyme activity, which can affect the metabolic pathways of other compounds.
Cellular Effects
The effects of this compound on cellular processes are profound. It influences cell function by affecting cell signaling pathways, gene expression, and cellular metabolism. For example, it has been shown to modulate the activity of certain kinases involved in cell signaling, leading to altered gene expression patterns . This modulation can result in changes in cellular metabolism, affecting the overall function of the cell.
Molecular Mechanism
At the molecular level, this compound exerts its effects through specific binding interactions with biomolecules. It can inhibit or activate enzymes by binding to their active sites, leading to changes in their activity . Additionally, it can influence gene expression by interacting with transcription factors or other regulatory proteins, thereby altering the transcriptional activity of specific genes.
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound can change over time. The compound’s stability and degradation are critical factors that influence its long-term effects on cellular function. Studies have shown that it remains stable under specific storage conditions but may degrade over time, leading to reduced efficacy . Long-term exposure to the compound in in vitro or in vivo studies has revealed potential changes in cellular function, including alterations in metabolic activity and gene expression.
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. At lower doses, the compound may exhibit beneficial effects, such as modulation of enzyme activity or gene expression . At higher doses, it can cause toxic or adverse effects, including cellular damage or disruption of normal metabolic processes. Threshold effects have been observed, indicating that there is a specific dosage range within which the compound is effective without causing harm.
Metabolic Pathways
This compound is involved in several metabolic pathways. It interacts with enzymes such as cytochrome P450, which play a crucial role in the metabolism of various compounds . These interactions can affect metabolic flux and alter the levels of specific metabolites, leading to changes in cellular metabolism.
Transport and Distribution
The transport and distribution of this compound within cells and tissues are mediated by specific transporters and binding proteins . These interactions influence the localization and accumulation of the compound, affecting its overall activity and function. The compound’s distribution can vary depending on the tissue type and the presence of specific transporters.
Subcellular Localization
This compound exhibits specific subcellular localization patterns. It may be directed to particular compartments or organelles within the cell through targeting signals or post-translational modifications . This localization can influence the compound’s activity and function, as it may interact with specific biomolecules within these compartments.
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride typically involves the reaction of 2,4-difluorobenzaldehyde with piperidine in the presence of an oxime-forming reagent . The reaction is carried out under inert gas (nitrogen or argon) at temperatures ranging from 2-8°C . The product is then purified through crystallization to obtain the hydrochloride salt form .
Industrial Production Methods
Industrial production of this compound follows similar synthetic routes but on a larger scale. The process involves the use of automated reactors and purification systems to ensure high yield and purity . The reaction conditions are carefully controlled to maintain consistency and quality of the final product .
Chemical Reactions Analysis
Types of Reactions
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized to form corresponding ketones or carboxylic acids.
Reduction: Reduction reactions can convert the oxime group to an amine.
Substitution: The compound can undergo nucleophilic substitution reactions, particularly at the fluorine atoms.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include potassium permanganate (KMnO4) and chromium trioxide (CrO3).
Reduction: Reducing agents such as lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4) are used.
Substitution: Nucleophiles like sodium methoxide (NaOMe) and potassium tert-butoxide (KOtBu) are commonly employed.
Major Products
Oxidation: Produces ketones or carboxylic acids.
Reduction: Forms amines.
Substitution: Results in various substituted derivatives depending on the nucleophile used.
Scientific Research Applications
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride has several scientific research applications:
Comparison with Similar Compounds
Similar Compounds
- (4-Fluorophenyl)(piperidin-4-yl)methanone hydrochloride
- (2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime
Uniqueness
(2,4-Difluorophenyl)(piperidin-4-yl)methanone oxime hydrochloride is unique due to its specific substitution pattern on the phenyl ring and the presence of the oxime group. This structural uniqueness contributes to its distinct chemical and biological properties, making it a valuable compound in pharmaceutical research and development .
Properties
IUPAC Name |
(NE)-N-[(2,4-difluorophenyl)-piperidin-4-ylmethylidene]hydroxylamine;hydrochloride |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C12H14F2N2O.ClH/c13-9-1-2-10(11(14)7-9)12(16-17)8-3-5-15-6-4-8;/h1-2,7-8,15,17H,3-6H2;1H/b16-12+; |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
CPVWKXXFKMUDPA-CLNHMMGSSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1CNCCC1C(=NO)C2=C(C=C(C=C2)F)F.Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C1CNCCC1/C(=N\O)/C2=C(C=C(C=C2)F)F.Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H15ClF2N2O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
276.71 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
135634-18-3 |
Source
|
| Record name | Methanone, (2,4-difluorophenyl)-4-piperidinyl-, oxime, hydrochloride (1:1) | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.113.612 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
Synthesis routes and methods
Procedure details
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