317323-77-6

Basic information

• Product Name: trans-(-)-4-(4-Fluorophenyl)-1-methyl-3-[(4-toluenesulfonyloxy)methyl]piperidine
• Synonyms: 3-PIPERIDINEMETHANOL, 4-(4-FLUOROPHENYL)-1-METHYL-, 4-METHYLBENZENESULFONATE (ESTER), (3S,4R)-;(-)-TRANS-4-(4-FLUOROPHENYL)-1-METHYL-3-[(4-TOLUENESULFONYLOXY)METHYL]PIPERIDINE;Trans-(-)-4-(4Fluorophenyl)-1-methyl-3-[(4-toluenesulfonylox)methyl]piperidine;3-PIPERIDINEMETHANOL,4-(4-FLUOROPHENYL)-1-METHYL-,4-METHYLBENZENESULFONATE(ESTER);3-Piperidinemethanol, 4-(4-fluorophenyl)-1-methyl-, 3-(4-methylbenzenesulfonate), (3S,4R)-;(3S,4R)-4-(4-Fluorophenyl)-1-methyl-3-piperidinemethanol 3-(4-Methylbenzenesulfonate);(3S,4R)-4-(4-Fluorophenyl)-1-methyl-3-piperidinemethanol Tosylate;Paroxol Tosylate
• CAS NO: 317323-77-6
• Molecular Formula: C₂₀H₂₄FNO₃S
• Molecular Weight: 377.47
• Product Categories: API intermediates;Aromatics;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 317323-77-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 117-118°C
• Boiling Point: 496.23 °C at 760 mmHg
• Flash Point: 253.911 °C
• Appearance: Brown Solid
• Density: 1.195 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly), Met
• CAS DataBase Reference: trans-(-)-4-(4-Fluorophenyl)-1-methyl-3-[(4-toluenesulfonyloxy)methyl]piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(-)-4-(4-Fluorophenyl)-1-methyl-3-[(4-toluenesulfonyloxy)methyl]piperidine(317323-77-6)
• EPA Substance Registry System: trans-(-)-4-(4-Fluorophenyl)-1-methyl-3-[(4-toluenesulfonyloxy)methyl]piperidine(317323-77-6)

Safety Data

• Hazardous Substances Data: 317323-77-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Different sources of media describe the Uses of 317323-77-6 differently. You can refer to the following data:
1. Piperidine derivative intermediate for paroxetin preparation
2. Piperidine derivative intermediate for paroxetin preparation.

InChI:InChI=1/C20H24FNO3S/c1-15-3-9-19(10-4-15)26(23,24)25-14-17-13-22(2)12-11-20(17)16-5-7-18(21)8-6-16/h3-10,17,20H,11-14H2,1-2H3/t17-,20-/m1/s1

Upstream product

• 598-56-1 N,N-dimethyl-ethanamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 318279-38-8 trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl piperidine 

Downstream Products

• 110429-36-2 (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine 
• 600135-84-0 (3S,4R)-3-(3,4-dibenzyloxyphenoxymethyl)-4-(4-fluorophenyl)-1-vinyloxypiperidine 
• 600135-88-4 (3S,4R)-3-(3,4-dibenzyloxyphenoxymethyl)-4-(4-fluorophenyl)-piperidine 
• 600135-86-2 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)-1-vinyloxycarbonylpiperidine 
• 600135-89-5 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)piperidine 
• 600135-90-8 (3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine 
• 112058-90-9 Brl 36610 
• 159126-30-4 Desmethylene-Paroxetine 
• 61869-08-7 paroxetine 
• 600135-83-9 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)-1-methylpiperidine 
• 600135-82-8 (3S,4R)-3-(3,4-dibenzyloxyphenoxymethyl)-4-(4-fluorophenyl)-1-methylpiperidine 

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.

Novel process

A process for the preparation of a compound of formula (1): in which R1 is an alkyl, arylalkyl, allyl, alkyloxycarbonyl, arylalkyloxycarbonyl, acyl or alkynyl group; and R2 is substituted phenyl, especially 3,4-methylenedioxyphenyl; and X is hydrogen or a readily removable group, such as chlorine, bromine or iodine.