112058-90-9

Basic information

• Product Name: 4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine
• Synonyms: 4-(4-FLUOROPHENYL)-3-(4-HYDROXY-3-METHOXYPHENOXYMETHYL)PIPERIDINE;4-[[(3S,4R)-4-(4-Fluorophenyl)piperidin-3-yl]methoxy]-2-methoxyphenol;(-)-trans-4-[4-(4’-Fluorophenyl)-3-piperidinylmethoxy]-2-methoxyphenol (Paroxetine metabolite);4-[[(3S,4R)-4-(4-Fluorophenyl)-3-piperidinyl]Methoxy]-2-Methoxy-phenol;BRL 36610A;Paroxetine 4-Hydroxy Metabolite;(-)-TRANS-4-[4-(4'-FLUOROPHENYL)-3-PIPERIDINYLMETHOXY]-2-METHOXYPHENOL, HYDROCHLORIDE;(-)-trans-4-[4-(4Fluorophenyl)-3-piperidinylmethoxy]-2-methoxyphenol,HCl
• CAS NO: 112058-90-9
• Molecular Formula: C19H22FNO3
• Molecular Weight: 331.38
• Product Categories: Metabolites;Paroxetine
• Mol File: 112058-90-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 189-1920C
• Boiling Point: 488.3 °C at 760 mmHg
• Flash Point: 249.1 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: 4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine(112058-90-9)
• EPA Substance Registry System: 4-(4-Fluorophenyl)-3-(4-hydroxy-3-methoxyphenoxymethyl)piperidine(112058-90-9)

Safety Data

• Hazardous Substances Data: 112058-90-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Tan Solid

Uses

A metabolite of Paroxetine

InChI:InChI=1/C19H22FNO3/c1-23-19-10-16(6-7-18(19)22)24-12-14-11-21-9-8-17(14)13-2-4-15(20)5-3-13/h2-7,10,14,17,21-22H,8-9,11-12H2,1H3

Upstream product

• 600135-89-5 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)piperidine 
• 40232-88-0 4-benzyloxy-3-methoxyphenol 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 600135-86-2 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)-1-vinyloxycarbonylpiperidine 
• 600135-83-9 (3S,4R)-4-(4-fluorophenyl)-3-(3-methoxy-4-benzyloxyphenoxymethyl)-1-methylpiperidine 
• 317323-77-6 ((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate 

Relevant articles and documents

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.