253768-88-6

Basic information

• Product Name: phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate
• Synonyms: (3S-trans) Phenyl-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-piperidinecarboxylate; 1-piperidinecarboxylic acid, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, phenyl ester, (3S,4R)-; 430-510-2; Phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate; T56 BO DO CHJ GO1- CT6NTJ AVOR& DR DF & & (3S-trans)- Form
• CAS NO: 253768-88-6
• Molecular Formula: C₂₆H₂₄FNO₅
• Molecular Weight: 449.4709
• EINECS: 430-510-2
• Mol File: 253768-88-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 574.766°C at 760 mmHg
• Flash Point: 301.408°C
• Density: 1.285g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate(253768-88-6)
• EPA Substance Registry System: phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate(253768-88-6)

Safety Data

• Hazardous Substances Data: 253768-88-6(Hazardous Substances Data)

Usage

General Description

The chemical compound phenyl (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate is a piperidine derivative containing a benzodioxol group and a fluoro substituted phenyl group. It is commonly used in medicinal research as a potential therapeutic agent due to its pharmacological properties. The compound's structure and functional groups make it suitable for binding to specific receptors and enzymes within the body, which could potentially have beneficial effects in the treatment of certain medical conditions. Further research and testing are needed to fully understand the potential uses and effects of this chemical compound.

Upstream product

• 1885-14-9 phenyl chloroformate 
• 110429-36-2 (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 317323-78-7 paroxetinemethylchloride carbamate 
• 459-57-4 4-fluorobenzaldehyde 
• 109887-52-7 C₁₅H₁₆FNO₄ 

Downstream Products

• 217797-14-3 paroxetine mesylate 
• 61869-08-7 paroxetine 
• 110429-35-1 (-)-paroxetine hydrochloride 

Relevant articles and documents

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.

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.