(3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine

Base Information

• Chemical Name: (3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine
• CAS No.: 324024-00-2
• Molecular Formula: C₁₉H₂₁NO₃
• Molecular Weight: 311.381
• UNII: AT4YDK3T53
• DSSTox Substance ID: DTXSID701157122
• Nikkaji Number: J513.265G
• ChEMBL ID: CHEMBL3991430
• Mol file: 324024-00-2.mol

Synonyms:Desfluoroparoxetine;AT4YDK3T53;UNII-AT4YDK3T53;324024-00-2;(3S,4R)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-phenylpiperidine;(3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine;Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-phenyl-, (3S,4R)-;(3S,4R)-3-[[(1,3-Benzodioxol-5-yl)oxy]methyl]-4-phenylpiperidine;Desfluoro Paroxetine impurity A;SCHEMBL5905364;CHEMBL3991430;DTXSID701157122;CS-O-14596;112058-81-8;LS-187370;CS-0165668;Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-phenyl-, trans-(-)-;(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-phenylpiperidine? (Paroxetine Impurity pound(c)

Chemical Property of (3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine

Chemical Property:

• Melting Point: 79-81°C
• PSA: 39.72000
• LogP: 4.31820
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 311.15214353
• Heavy Atom Count: 23
• Complexity: 372

Purity/Quality:

98%Min ^*data from raw suppliers

Defluoro Paroxetine, Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC(C1C2=CC=CC=C2)COC3=CC4=C(C=C3)OCO4
• Isomeric SMILES: C1CNC[C@H]([C@@H]1C2=CC=CC=C2)COC3=CC4=C(C=C3)OCO4

Technology Process of (3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine

There total 3 articles about (3S,4R)-3-(((1,3-Benzodioxol-5-yl)oxy)methyl)-4-phenylpiperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(-)-paroxetine hydrochloride (110429-35-1,130855-30-0) → desfluoro paroxetine (324024-00-2)

Guidance literature:

With sodium hydroxide; palladium on activated charcoal; In isopropyl alcohol; at 82 ℃; for 3h;

DOI:10.1016/j.bmcl.2004.04.018

Reference yield: 29.0%

paroxetine (61869-08-7) → desfluoro paroxetine (324024-00-2)

Guidance literature:

With 2-methyl-propan-1-ol; methanesulfonato(2-dicyclohexylphosphino -2’,6’-di-i-propoxy-1,1‘-biphenyl)(2’-amino-1,1’-biphenyl-2-yl)palladium(II); sodium tert-pentoxide; In toluene; at 80 ℃; for 72h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00889

Reference yield:

→ (+/-)trans-4-phenyl-3-(3,4-methylenedioxyphenoxymethyl)-piperidine (324024-00-2) + 4-(4-Fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine

Guidance literature:

upstream raw materials:

(-)-paroxetine hydrochloride

paroxetine

Refernces

• 1、 Gair, Joseph J.,Grey, Ronald L.,Giroux, Simon,Brodney, Michael A.. "Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes". supporting information. p. 2482 - 2487. Retrieved 2019/04/10.
• 2、 -. "Etherification and dealkylation of piperidine derivatives and intermediates". . . Retrieved 2008/06/13.