600135-84-0

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 3-[[3,4-bis(phenylmethoxy)phenoxy]methyl]-4-(4-fluorophenyl)-, ethenyl ester, (3S,4R)-
• CAS NO: 600135-84-0
• Molecular Formula: C35H34FNO5
• Molecular Weight: 567.657
• Mol File: 600135-84-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 3-[[3,4-bis(phenylmethoxy)phenoxy]methyl]-4-(4-fluorophenyl)-, ethenyl ester, (3S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 3-[[3,4-bis(phenylmethoxy)phenoxy]methyl]-4-(4-fluorophenyl)-, ethenyl ester, (3S,4R)-(600135-84-0)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 3-[[3,4-bis(phenylmethoxy)phenoxy]methyl]-4-(4-fluorophenyl)-, ethenyl ester, (3S,4R)-(600135-84-0)

Safety Data

• Hazardous Substances Data: 600135-84-0(Hazardous Substances Data)

Upstream product

• 317323-77-6 ((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 27688-86-4 3,4-dibenzyloxyphenol 
• 5130-24-5 Vinyl chloroformate 
• 600135-82-8 (3S,4R)-3-(3,4-dibenzyloxyphenoxymethyl)-4-(4-fluorophenyl)-1-methylpiperidine 

Downstream Products

• 159126-30-4 Desmethylene-Paroxetine 
• 600135-88-4 (3S,4R)-3-(3,4-dibenzyloxyphenoxymethyl)-4-(4-fluorophenyl)-piperidine 

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.