110429-36-2

Usage

Uses

Used in Pharmaceutical Industry:
N-Methylparoxetine is used as a drug impurity for Paroxetine, a selective serotonin reuptake inhibitor. It plays a role in the manufacturing process of Paroxetine, which is a medication used to treat various mental health disorders such as depression, anxiety, and obsessive-compulsive disorder.
As a drug impurity, N-Methylparoxetine is essential in the development and production of Paroxetine, ensuring the quality and efficacy of the final product. It is important to control the levels of this impurity to maintain the safety and effectiveness of the medication.

InChI:InChI=1/C20H22FNO3/c1-22-9-8-18(14-2-4-16(21)5-3-14)15(11-22)12-23-17-6-7-19-20(10-17)25-13-24-19/h2-7,10,15,18H,8-9,11-13H2,1H3

Upstream product

• 533-31-3 Sesamol 
• 317323-77-6 ((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate 
• 110429-35-1 (-)-paroxetine hydrochloride 
• 74-88-4 methyl iodide 
• 1258537-32-4 trans 4-(p-fluorophenyl)-3-(p-toluenesulfonyloxymethyl)-N-methylpiperidine 
• 109887-52-7 C₁₅H₁₆FNO₄ 
• 459-57-4 4-fluorobenzaldehyde 
• 124-38-9 carbon dioxide 
• 61869-08-7 paroxetine 
• 50-00-0 formaldehyd 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 

Downstream Products

• 61869-08-7 paroxetine 
• 317323-78-7 paroxetinemethylchloride carbamate 
• 253768-88-6 (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylic acid phenyl ester 
• 246850-71-5 (3S,4R)-trans-1-benzyloxycarbonyl-4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine 
• 110429-35-1 (-)-paroxetine hydrochloride 
• 533935-67-0 N-formyl paroxetine ((3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carbaldehyde) 
• 72471-80-8 [(-)-(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxy)phenoxymethyl]piperidine acetate 
• 600135-90-8 (3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine 

Related news

Stereoselectiveseparation of racemic trans-paroxol, N-Methylparoxetine (cas 110429-36-2) and paroxetine containing two chiral carbon centres by countercurrent chromatography08/11/2019

Racemic trans-paroxol, trans-N-methylparoxetine and trans-paroxetine containing two chiral centres were stereoselectively separated using countercurrent chromatography with hydroxypropyl-β-cyclodextrin as the chiral selector. A two-phase solvent system composed of n-butyl acetate and 0.1 mol L−...detailed

Relevant academic research and scientific papers

Structural differences between paroxetine and femoxetine responsible for differential inhibition of Staphylococcus aureus efflux pumps

In this study the chemical modification of paroxetine was employed to determine which structural differences between the paroxetine-like and femoxetine-like selective serotonin reuptake inhibitors is responsible for the differential potency of these agent

Pharmacophore modeling, docking and the integrated use of a ligand- And structure-based virtual screening approach for novel DNA gyrase inhibitors: Synthetic and biological evaluation studies

Fluoroquinolones, a class of compound, act via inhibiting DNA gyrase and topoisomerase IV enzymes. This is an important class of drugs with high success rates for the treatment of tuberculosis and other bacterial infections. An indirect drug design approach was used to develop a meaningful pharmacophore model using the HypoGen module of Discovery Studio 2.0 on a set of 27 structurally diverse compounds with a wide range of biological activity (5 log units). The best hypothesis had three hydrogen bond acceptors (HBA) and one hydrophobic (Hy) moiety, showing r = 0.95, and it predicts the test set of 44 compounds well, with r2 = 0.823. The same features (acceptor and hydrophobic functionality) were validated at the binding site of the DNA gyrase active site using GOLD version 3.0.1 and Molegro Virtual Docker, which showed corresponding hydrogen bond interactions and also π-π stacking interactions that correlated well with the PIC50 values (r2 = 0.6142). The thoroughly validated model was used to screen an extensive database of 0.25 million compounds to identify potential leads. The validated model was implemented for the identification, design, synthesis, and biological evaluation of leads. Ten new chemical entities were synthesized based on our scaffold hopping techniques from the identified virtual screening and tested against the tuberculosis bacterium to obtain preliminary MIC values. The results showed that 3 out of 10 synthesized compounds exhibited good MICs, from 1.25 to 50 μM. This proves the robustness and applicability of the developed model, which is a promising tool for identifying new topoisomerase II inhibitors for the treatment of tuberculosis.

Iron-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2

We herein describe an efficient iron-catalyzed selective N-methylation and N-formylation of amines with CO2 and silane using mono-phosphine as ligand. With commercially available [CpFe(CO)2]2 as catalyst, Fe-catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe-catalyzed formylation of amines was realized at a lower temperature. The method was successfully applied in the late-stage methylation and formylation of drug molecules containing amine moiety. (Figure presented.).

Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles

N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.

Improved process for paroxetine hydrochloride substantially free from potential impurities

An efficient process for production of paroxetine hydrochloride hemihydrate 1, a selective 5-hydroxytryptamine (serotonin) reuptake inhibitor, is described. Identification and control of potential impurities and establishment of efficient downstream workup procedures enabled us to produce paroxetine hydrochloride hemihydrate 1 efficiently.

A PROCESS FOR THE PREPARATION OF (-)-TRANS-4-(P-FLUOROPHENYL)-3-[[3,4-(METHYLENEDIOXY)PHENOXY]METHYL)]PIPERIDINE

A process for preparing (-)-trans-4-(4-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]-piperidine, a compound of formula (I) or pharmaceutically acceptable salts thereof, said process comprising hydrolyzing a compound of formula (II), wherein R may be selected from halo substituted or unsubstituted linear, branched or cyclic alkyl, alkylaryl, arylalkyl, by treatment with a base in a solvent system comprising a polar aprotic water miscible solvent and a hydrocarbon solvent wherein the polar aprotic water miscible solvent is selected from a sulfoxide solvent, an amide solvent or mixture thereof.

PIPERIDINE COMPOUNDS AND PROCESS FOR PROVIDING SUCH

The tosylate ester of the formula (6) and its salts, are convenient intermediates in the synthesis of paroxetine.

Preparation of paroxetine involving novel intermediates

Disclosed are processes for preparing novel carbamate intermediates of paroxetine comprising dealkylating N-alkylparoxetine by reaction thereof with a haloalkyl ester of a haloformic acid, in a suitable organic solvent. Also disclosed are processes for preparing paroxetine comprising hydrolyzing the novel carbamate intermediates in a suitable solvent. Paroxetine prepared by the above processes can be neutralized with hydrogen chloride and crystallized as paroxetine hydrochloride anhydrous, hemihydrate or as a solvate of isopropanol. The invention is further directed to the novel carbamate intermediates formed by the disclosed processes.

Synthesis of the major metabolites of Paroxetine

Paroxetine is a well-known antidepressant, used worldwide in therapeutics. In comparison with other selective serotonin reuptake inhibitors, it exhibits the highest activity in serotonin reuptake inhibition. Paroxetine metabolism initially involves its demethylenation to the catechol intermediate, which is then O-methylated at positions C3 or C4. Herein, the chemistry resulting in the syntheses of these metabolites (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine and (3S,4R)-4-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine is described starting from the common intermediate (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine. Additionally, the common intermediate was used to synthesize paroxetine, which had the same structure and stereochemistry as commercial paroxetine, thereby confirming our synthetic route.

Preparation of N-methylparoxetine and related intermediate compounds

The present invention provides a process for preparing N-methylparoxetine, an intermediate in the synthesis of paroxetine, by reacting sesamol-tetrabutylammonium salt with CIPMA. The synthesis of the intermediate in the prior are resulted in a particularl