trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol

Base Information

• Chemical Name: trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol
• CAS No.: 201855-60-9
• Molecular Formula: C19H22FNO
• Molecular Weight: 299.388
• UNII: BCZ79F59E9
• DSSTox Substance ID: DTXSID80446987
• Nikkaji Number: J1.554.283G
• Wikidata: Q82265749
• Mol file: 201855-60-9.mol

Synonyms:201855-60-9;trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol;((3S,4R)-1-Benzyl-4-(4-fluorophenyl)piperidin-3-yl)methanol;BCZ79F59E9;[(3S,4R)-1-BENZYL-4-(4-FLUOROPHENYL)PIPERIDIN-3-YL]METHANOL;3-Piperidinemethanol, 4-(4-fluorophenyl)-1-(phenylmethyl)-, (3S,4R)-;(-)-trans-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)piperidine;(-)-trans-1-Benzyl-4-(4-fluorophenyl)-3-hydroxymethylpiperidine;(-)-(3S,4R)-4-(4-Fluorophenyl)-1-(phenylmethyl)-3-piperidinemethanol;starbld0000540;UNII-BCZ79F59E9;SCHEMBL4030955;DTXSID80446987;(3S,4R)-4-(4-Fluorophenyl)-1-(phenylmethyl)-3-piperidinemethanol;CS-0165665;EN300-197673;EN300-1266461;Paroxetine Hydrochloride Anhydrous EP Impurity H;1-Benzyl-4alpha-(4-fluorophenyl)piperidine-3beta-methanol;rac-[(3R,4S)-1-benzyl-4-(4-fluorophenyl)piperidin-3-yl]methanol;trans-(4R)-1-benzyl-4-(4'-fluorophenyl)-3-hydroxymethylpiperidine;((3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidin-3-yl)methanol? (Paroxetine Impurity pound(c);N-Benzyl Paroxol;[(3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidin-3-yl]methanol

Chemical Property of trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol

Chemical Property:

• Vapor Pressure: 3.45E-07mmHg at 25°C
• Melting Point: >55oC (dec.)
• Boiling Point: 402.1oC at 760 mmHg
• Flash Point: 197oC
• PSA: 23.47000
• Density: 1.139g/cm3
• LogP: 3.36160
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 299.16854249
• Heavy Atom Count: 22
• Complexity: 323

Purity/Quality:

99.0% Min ^*data from raw suppliers

trans1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC(C1C2=CC=C(C=C2)F)CO)CC3=CC=CC=C3
• Isomeric SMILES: C1CN(C[C@H]([C@@H]1C2=CC=C(C=C2)F)CO)CC3=CC=CC=C3
• Uses: Paroxetine intermediate

Technology Process of trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol

There total 45 articles about trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol 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: 100.0%

isobutyl (3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidine-3-carboxylate (369593-39-5) → (3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol (201855-60-9,188869-25-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.833333h;

DOI:10.1016/S0040-4039(01)01096-6

Reference yield: 86.0%

(3S,4R)-ethyl 1-benzyl-4-(4-fluorophenyl)-6-hydroxy-2-oxopiperidine-3-carboxylate (323203-13-0) → (3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol (201855-60-9,188869-25-2)

Guidance literature:

With borane-THF; In tetrahydrofuran;

DOI:10.1016/j.tet.2011.08.079

Reference yield: 76.0%

(3S,4R)-1-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-fluoro-phenyl)-piperidine → (3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol (201855-60-9,188869-25-2)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1016/j.tetlet.2004.08.174

upstream raw materials:

isobutyl (3S,4R)-1-benzyl-4-(4-fluorophenyl)piperidine-3-carboxylate

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylic acid methyl ester

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester

malonic acid dibenzyl ester

Downstream raw materials:

paroxetine

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine

Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester

Refernces

• 1、 Zhang, Yu,Liao, Yuting,Liu, Xiaohua,Yao, Qian,Zhou, Yuhang,Lin, Lili,Feng, Xiaoming. "Catalytic Michael/Ring-Closure Reaction of α,β-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (?)-Paroxetine". . p. 15119 - 15124. Retrieved 2016/10/11.
• 2、 ?íhalová, Sylva,Valero, Guillem,Schimer, Ji?í,Humpl, Marek,Dra?ínsky, Martin,Moyano, Albert,Rios, Ramon,Vesely, Jan. "Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines". scheme or table. p. 8942 - 8950. Retrieved 2011/12/01.