N-Methylparoxetine

Base Information

• Chemical Name: N-Methylparoxetine
• CAS No.: 110429-36-2
• Molecular Formula: C20H22FNO3
• Molecular Weight: 343.398
• European Community (EC) Number: 924-787-3,600-963-2
• UNII: 3X658583PO
• DSSTox Substance ID: DTXSID20149243
• Nikkaji Number: J425.849E
• Wikidata: Q27166378
• ChEMBL ID: CHEMBL322363
• Mol file: 110429-36-2.mol

Synonyms:N-Methylparoxetine;110429-36-2;N-Methyl Paroxetine;Methylparoxetine;UNII-3X658583PO;3X658583PO;(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine;(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)-1-methylpiperidine;(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methyl-piperidine;trans(-)-1-Methyl-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine;(3S,4R)-N-Methylparoxetine;CPD000469181;MLS001424004;trans-(-)-N-methylparoxetine;CHEMBL322363;CHEBI:94536;DTXSID20149243;MOJZPKOBKCXNKG-YJBOKZPZSA-N;HMS2051I12;BCP13507;MFCD03788781;AKOS015851047;AKOS015889696;CCG-100867;NC00117;(-)-trans-4-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-methylpiperidine;AC-18943;SMR000469181;CS-0165673;M2645;T71590;J-002423;BRD-K19277754-001-01-4;Q27166378;(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine;(3S,4R)-3-((BENZODIOXOL-5-YLOXY)METHYL)-4-(4-FLUOROPHENYL)-1-METHYLPIPERIDINE;(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine;(3S-trans)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine;Piperidina, 3-[(1,3-benzodioxol-5-iloxi)metil]-4-(4-fluorofenil)-1-metil-, (3s,4r)-;Piperidine,3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methyl-,(3S,4R)-;(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine? (Paroxetine Impurity pound(c);PIPERIDINE, 3-((1,3-BENZODIOXOL-5-YLOXY)METHYL)-4-(4-FLUOROPHENYL)-1-METHYL-, (3S,4R)-;PIPERIDINE, 3-((1,3-BENZODIOXOL-5-YLOXY)METHYL)-4-(4-FLUOROPHENYL)-1-METHYL-, (3S-TRANS)-;Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methyl-, (3S,4R)-;Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methyl-, (3S-trans)-;BRL-42493;Paroxetine Related Compound F

Chemical Property of N-Methylparoxetine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 109.0 to 113.0 °C
• Refractive Index: 1.562
• Boiling Point: 443.709 °C at 760 mmHg
• PKA: 8.48±0.20(Predicted)
• Flash Point: 222.147 °C
• PSA: 30.93000
• Density: 1.198 g/cm³
• LogP: 3.60660
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 343.15837173
• Heavy Atom Count: 25
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

N-Methyl Paroxetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(C(C1)COC2=CC3=C(C=C2)OCO3)C4=CC=C(C=C4)F
• Isomeric SMILES: CN1CC[C@H]([C@@H](C1)COC2=CC3=C(C=C2)OCO3)C4=CC=C(C=C4)F
• Uses: A drug impurity of Paroxetin, a selective serotonin reuptake inhibitor. Paroxetine USP Related Compound F. A drug impurity of Paroxetin, a selective serotonin reuptake inhibitor.

Technology Process of N-Methylparoxetine

There total 14 articles about N-Methylparoxetine 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: 95.0%

1-(2-chloroethoxycarbonyl)-4-fluorophenyl-3-[5-(1,3-dioxaindanyl)oxymethyl]piperidine + 2-chloroethyl carbamate of paroxetine + paroxetine (61869-08-7) → (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine (110429-36-2)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 92.0%

(-)-paroxetine hydrochloride (110429-35-1,130855-30-0) + methyl iodide (74-88-4) → (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine (110429-36-2)

Guidance literature:

With potassium carbonate; In acetonitrile; for 5h; Heating;

DOI:10.1016/j.bmcl.2004.04.018

Reference yield: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + paroxetine (61869-08-7) → (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine (110429-36-2)

Guidance literature:

With formic acid; triethylamine; In water; tert-butyl alcohol; at 100 ℃; for 14h;

DOI:10.1002/cctc.201701617

upstream raw materials:

Sesamol

((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

(-)-paroxetine hydrochloride

methyl iodide

Downstream raw materials:

(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine

paroxetine

paroxetinemethylchloride carbamate

[(-)-(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxy)phenoxymethyl]piperidine acetate

Refernces

• 1、 Ahmad, Irfan,Balaramnavar, Vishal M.,Gupta, Madan M.,Jawaid, Talha,Kamal, Mehnaz,Kumar, Santosh,Masand, Mukesh,Mathpal, Deepti,Saeed, Mohd,Sharma, Pramod K.,Srivastava, Swayam Prakash,Thomas, Anisha,Zaman, Gaffar Sarwar. "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". . p. 34462 - 34478. Retrieved 2021/12/01.
• 2、 Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.. "Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles". . p. 1235 - 1240. Retrieved 2018/02/09.