(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine

Base Information

• Chemical Name: (3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine
• CAS No.: 105812-81-5
• Molecular Formula: C13H18FNO
• Molecular Weight: 223.29
• Hs Code.: 29333999
• European Community (EC) Number: 406-030-4,415-550-0,600-679-9
• UNII: QRA30YT0AV,IDR7471BR7
• DSSTox Substance ID: DTXSID90909750,DTXSID701335734
• Nikkaji Number: J1.182.747K
• Wikidata: Q76146107
• ChEMBL ID: CHEMBL4971536
• Mol file: 105812-81-5.mol

Synonyms:105812-81-5;(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine;Paroxol;(3S,4R)-4-(4-Fluorophenyl)-1-methyl-3-piperidinemethanol;[(3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl]methanol;109887-53-8;UNII-QRA30YT0AV;QRA30YT0AV;3-Piperidinemethanol, 4-(4-fluorophenyl)-1-methyl-, (3S,4R)-;UNII-IDR7471BR7;IDR7471BR7;((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methanol;MFCD06658161;(+/-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine;4-(4'-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, (-)-trans-;4-(4-Fluorophenyl)-3-(hydroxymethyl)-1-methylpiperidine, (+/-)-trans-;EC 406-030-4;EC 415-550-0;(-)-trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine;Trans-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methyl-piperidine;(3S)-4-(4'-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine;(-)-Paroxol;TRANS-PAROXOL;(+/-)-PAROXOL;SCHEMBL1944023;PAROXOL, TRANS-(-)-;(+/-)-TRANS-4-(FLUOROPHENYL)-3-HYDROXYMETHYL-1-METHYLPIPERIDINE;CHEMBL4971536;Paroxol 1.0 mg/ml in Methanol;PAROXOL, (+/-)-;DTXSID90909750;CXRHUYYZISIIMT-AAEUAGOBSA-N;[(3S,4R)-4-(4-fluorophenyl)-1-methyl-3-piperidyl]methanol;AM683;DTXSID701335734;PAROXOL, TRANS-(+/-)-;(3S,4R)-[4-(4-Fluoro-phenyl)-1-methyl-piperidin-3-yl]-methanol;MFCD03411902;AKOS015853527;AKOS015895971;AC-8186;CS-W003303;FS-2563;FS-3020;AC-11787;AC-16240;F0878;J-501283;J-513513;((3S)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methanol;(4R,3S)-4-(4-Fluorophenyl)-1-methyl-3-piperidinemethanol;1-Methyl-4alpha-(4-fluorophenyl)piperidine-3beta-methanol;(3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1methylpiperidine;(3S-trans)-4-(4-Fluorophenyl)-1-methyl-3-piperidinemethanol;(+/-) trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine;(+/-)-trans-4-(4'-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine;(+/-)-trans-4-(4'fluorophenyl)-3-hydroxymethyl-N-methyl piperidine;(-)-trans-4-(4'-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine;(-)-trans-4-(4-fluorophenyl)-1-methyl-3-hydroxymethylpiperidine;(-)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine;(4R,3S)-4-(4-Fluorophenyl)-3-hydroxymethyl-N-methylpiperidine;(+/-)-trans-[4-(4-fluorophenyl)-1-methyl-piperidin-3-yl]-methanol;(-)TRANS-4R-(4-FLUOROPHENYL)-3S-HYDROXYMETHYL-1-METHYLPIPERIDINE;(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine, AldrichCPR;3-PIPERIDINEMETHANOL, 4-(4-FLUOROPHENYL)-1-METHYL-, (3S-TRANS)-;3-PIPERIDINEMETHANOL, 4-(4-FLUOROPHENYL)-1-METHYL-, TRANS-(+/-)-;PIPERIDINEMETHANOL, 4-(4-FLUOROPHENYL)-1-METHYL-, (3R,4S)-REL-;TRANS-N-METHYL-4-(4-FLUOROPHENYL)-3-(HYDROXYMETHYL)PIPERIDINE;(+/-)-TRANS-4-(P-FLUOROPHENYL)-3-(HYDROXYMETHYL)-1-METHYLPIPERIDINE;TRANS-(4R,3S)-4-(4-FLUOROPHENYL)-3-HYDROXYMETHYL-1-METHYLPIPERIDINE;JLD

Chemical Property of (3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000504mmHg at 25°C
• Melting Point: 97-101 ºC
• Refractive Index: 1.518
• Boiling Point: 300.3 ºC at 760 mmHg
• PKA: 14.93±0.10(Predicted)
• Flash Point: 135.4 ºC
• PSA: 23.47000
• Density: 1.092 g/cm³
• LogP: 1.79120
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 223.137242360
• Heavy Atom Count: 16
• Complexity: 216

Purity/Quality:

98% ^*data from raw suppliers

Paroxol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: N-Xn,N,Xn
• Statements: 51/53-41-22
• Safety Statements: 61-39-26-22-37/39-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(C(C1)CO)C2=CC=C(C=C2)F
• Isomeric SMILES: CN1CC[C@H]([C@@H](C1)CO)C2=CC=C(C=C2)F
• Uses: An intermediate in the synthesis of Paroxetine, a selective serotonin reuptake inhibitor. An intermediate in the synthesis of Paroxetine (P205750), a selective serotonin reuptake inhibitor.

Technology Process of (3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine

There total 6 articles about (3S,4R)-4-(4-Fluorophenyl)-3-hydroxymethyl-1-methylpiperidine 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: 80.0%

(3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2,109887-52-7) → (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine (105812-81-5)

Guidance literature:

(3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione; With lithium aluminium tetrahydride; In tetrahydrofuran; toluene; at 15 - 65 ℃;

With water; sodium hydroxide; In tetrahydrofuran; toluene; at 0 - 5 ℃; for 0.333333h;

DOI:10.1016/j.tetasy.2010.12.020

Reference yield: 80.0%

methyl (3S,4R)-4-(4-fluorophenyl)-6-hydroxy-1-methyl-2-oxopiperidine-3-carboxylate → (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine (105812-81-5)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at -10 - 30 ℃; for 6h; Temperature; Inert atmosphere;

Reference yield: 78.4%

(-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester (335158-58-2) → (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine (105812-81-5)

Guidance literature:

(-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester; With lithium aluminium tetrahydride; In tetrahydrofuran; at 10 ℃;

With sodium hydroxide; for 0.5h;

upstream raw materials:

(-)-(3S,4R)-4-(4-fluoro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester

(+/-)-trans-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-piperidine-3-carboxylic acid ethyl ester

(3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione

4-fluorocinnamic acid

Downstream raw materials:

(3S,4R)-trans-3-carbomethoxy-4-(4-fluorophenyl)-N-methyl-piperidine(-)-mandelicacid salt

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF PAROXETINE AND ITS INTERMEDIATE". Page/Page column 15. . Retrieved 2017/03/21.
• 2、 -. "ENANTIOSPECIFIC PROCESS FOR THE PREPARATION OF PAROXETINE INTERMEDIATE". Page 26. . Retrieved 2008/06/13.