130855-30-0

Basic information

• Product Name: PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE)
• Synonyms: PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE);(+)-trans-Paroxetine hydrochloride;Paroxetine Related CoMpound C;(3R,4S)-3-[(1,3-Benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)piperidine Hydrochloride;(3R-trans)-3-[(1,3-Benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)piperidine Hydrochloride;ent-Paroxetine Hydrochloride;(3R,4S)-3-[(1,3-benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)piperidine hydrochloride (aka Paroxetine iMpurity D);Paroxetine HCl EP IMp D (USP RC C)
• CAS NO: 130855-30-0
• Molecular Formula: C19H21ClFNO3
• Molecular Weight: 365.8263432
• EINECS: 208-028-7
• Product Categories: Aromatics;Heterocycles;Impurities;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 130855-30-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE)(CAS DataBase Reference)
• NIST Chemistry Reference: PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE)(130855-30-0)
• EPA Substance Registry System: PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE)(130855-30-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41-62
• Safety Statements: 26-39
• Hazardous Substances Data: 130855-30-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE) is used as an enantiomeric impurity for the development and quality control of Paroxetine (P205750). Its presence in the final drug product needs to be monitored and controlled to ensure the safety, efficacy, and purity of the medication. This is important because enantiomeric impurities can sometimes have different or even adverse effects compared to the main active ingredient.
Additionally, understanding the properties and behavior of PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE) can contribute to the optimization of the manufacturing process and the development of new, more effective medications with fewer side effects.

Upstream product

• 533-31-3 Sesamol 
• 61869-08-7 paroxetine 
• 147-71-7 D-tartaric acid 
• 459-57-4 4-fluorobenzaldehyde 
• 100332-09-0 4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine 
• 754206-43-4 (3R,4R)-1-benzyl-4-(4-fluorophenyl)-3-{[(methylsulfonyl)oxy]methyl}piperidine 
• 201855-64-3 (3R,4R)-1-benzyl-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine 
• 118798-76-8 tris(4-fluorophenyl)bismuth dichloride 
• 94923-25-8 1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one 
• 916214-12-5 3-(diphenoxy-phosphoryloxy)-4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-13-6 4-(4-fluoro-phenyl)-3-[(isopropoxy-dimethyl-silanyl)-methyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-14-7 4-(4-fluoro-phenyl)-3-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-01-2 1-benzyl-4-(4-fluoro-phenyl)-1,6-dihydro-2H-pyridin-3-one 
• 916214-03-4 4-(4-fluoro-phenyl)-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation

A total synthesis of paroxetine is reported, with a diastereoselective and diastereoconvergent cobalt-catalysed sp3-sp2 coupling reaction involving a 3-substituted 4-bromo-N-Boc-piperidine (Boc = tert-butoxycarbonyl) substrate as a key step. A 9:1 diastereoselectivity was obtained, while a control experiment involving a conformationally locked 3-substituted 4-bromo-tert-butyl cyclohexane ring proceeded with essentially complete stereoselectivity.

Diastereoconvergent Synthesis of (–)-Paroxetine

A diastereoconvergent approach to (–)-paroxetine from diastereomeric 3,4-epoxy-2-piperidones is reported. For this synthesis, a regioselective and stereodivergent CuI-catalyzed epoxide-ring-opening reaction of epoxyamide precursors to give the 4-(4-fluorophenyl)-2-piperidone skeleton with the correct absolute configuration is crucial. Using CuBr·SMe2 as a catalyst, the epoxide-ring-opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.

Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis

We describe the fully stereodivergent, dual catalytic α-allylation of linear aldehydes. The reaction proceeds via direct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter proved to be crucial for achieving high enantio- and diastereoselectivity (>99% ee, up to >20:1 dr). The utility of the method is demonstrated in a concise enantioselective synthesis of the antidepressant (-)-paroxetine.

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.

SULFATED GALACTANS WITH ANTITHROMBOTIC ACTIVITY, PHARMACEUTICAL COMPOSITION, METHOD FOR TREATING OR PROPHYLAXIS OF ARTERIAL OR VENOUS THROMBOSIS, METHOD OF EXTRACTION AND USE THEREOF

The present invention relates to low molecular weight sulfated galactans, obtained from algae, particularly genus Botryocladia, preferably species Botryocladia occidentallis, which have no effect on the factor XII activation of the clotting cascade, having antithrombotic heparinoid activity. The present invention also refers to a pharmaceutical composition comprising said sulfated galactans and the use thejreof, as heparin substitute, in the treatment or prophylaxis of arterial or venous thrombosis in humans and animals. Furthermore, the present invention provides a method of extraction of the said sulfated galactans.

Controlled Release Compositions of an Antidepressant Agent

The present invention relates to controlled release compositions comprising an anti-depressant compound. More particularly, the present invention relates to controlled release compositions comprising paroxetine hydrochloride.

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.

PREPARATION OF PAROXETINE HYDROCHLORIDE HEMIHYDRATE

A process for preparing paroxetine hydrochloride hemihydrate.

Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation

Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)3BiCl2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (β-phosphonio)enolate to provide the α-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki-Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (-)-paroxetine (PAXIL).

NOVEL FORM OF ANHYDROUS PAROXETINE HYDROCHLORIDE AND METHOD FOR PREPARATION THEREOF

A novel form of anhydrous Paroxetine hydrochloride is prepared by dissolving Paroxetine base in isopropanol, which is treated with a solution of hydrogen chloride in isopropanol. 50 to 60% of isopropanol used in the reaction is then distilled at atmospheric pressure. The product thus obtained after drying contains isopropanol not more than 3% and water content which is less than 2.0%. The product is found to be stable even after 3 days upon direct exposure to 75% RH at 40°C and the crystallinity of product is unchanged as confirmed by X-ray powder difractogram. The product is also found to be stable for three months as per ICH satiability conditions.