140235-25-2

Basic information

• Product Name: rac (2,3-Dimethoxyphenyl)-4-piperidinemethanol
• Synonyms: rac (2,3-Dimethoxyphenyl)-4-piperidinemethanol;rac (2,3-Dimethoxyphenyl)-
• CAS NO: 140235-25-2
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.32144
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 140235-25-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 404.8°C at 760 mmHg
• Flash Point: 198.6°C
• Appearance: /
• Density: 1.106g/cm³
• Vapor Pressure: 2.8E-07mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: rac (2,3-Dimethoxyphenyl)-4-piperidinemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: rac (2,3-Dimethoxyphenyl)-4-piperidinemethanol(140235-25-2)
• EPA Substance Registry System: rac (2,3-Dimethoxyphenyl)-4-piperidinemethanol(140235-25-2)

Safety Data

• Hazardous Substances Data: 140235-25-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C14H21NO3/c1-17-12-5-3-4-11(14(12)18-2)13(16)10-6-8-15-9-7-10/h3-5,10,13,15-16H,6-9H2,1-2H3

Upstream product

• 139290-70-3 tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 498-94-2 isonipecotic acid 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 280115-99-3 tert-butyl 4-(chlorocarbonyl)-piperidine-1-carboxylate 
• 243640-28-0 4-(2,3-dimethoxybenzoyl)pyridine 
• 243640-27-9 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine 
• 139290-71-4 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 139290-72-5 (2,3-dimethoxyphenyl)(piperidin-4-yl)methanone 
• 243640-26-8 tert-butyl 4-((2,3-dimethoxyphenyl)(hydroxy)methyl)piperidine-1-carboxylate 

Downstream Products

• 243640-19-9 (2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol 
• 311348-76-2 (S)-(-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol 
• 243640-37-1 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]-N-2-(4-fluorophen-1-oxo-ethyl)piperidine 
• 139290-69-0 (2,3-dimethoxy-phenyl)-{1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-methanol 
• 869749-09-7 (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt 
• 1160298-48-5 (2,3-dimethoxyphenyl)-(1-(2-p-tolylethyl)-piperidin-4-yl)-methanol 
• 126405-25-2 (2,3-dimethoxyphenyl)-(1-(2-p-methoxyphenylethyl)-piperidin-4-yl)-methanol 
• 1160298-47-4 (2,3-dimethoxyphenyl)-(1-(2-p-nitrophenylethyl)-piperidin-4-yl)-methanol 
• 1160298-46-3 (2,3-dimethoxyphenyl)-(1-(p-fluorobenzyl)-piperidin-4-yl)-methanol 
• 1186018-69-8 [⁽¹⁸⁾F]MDL 100907 
• 869749-10-0 (R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-anisoyl)tartaric acid salt 
• 175673-57-1 (-)-MDL 100907 
• 139290-65-6 R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol 

Relevant articles and documents

Synthesis of 11C-labelled amides by palladium-mediated carboxamination using [11C]carbon monoxide, in situ activated amines and 1,2,2,6,6-pentamethylpiperidine

Twenty-seven 11C-labelled amides were synthesised using [11C]carbon monoxide in low concentrations, palladium(0), organohalides and amines in a small micro-autoclave (200 μL). The focus of the study was to improve the radiochemical yields in this palladium-mediated amide synthesis when employing less-reactive amines, such as methylamine, [(2R)-1-ethylpyrrolidin-2-yl]methylamine (40) and 2-(pyridin-2-yl)ethanamine (41). The radiochemical yields were improved when utilizing 1,2,2,6,6-pentamethylpiperidine (pempidine) in combination with the amine substrates. The 11C-labelled amides were obtained mostly in high radiochemical yields (in the range 16-94%) and the specific radioactivity varied between 650 and 1250GBq/μmol. 1-(1,3-Benzodioxol-5-yl[13C]carbonyl)piperidine (6a) was synthesised to verify the labelling position (δ = 169.8 ppm) using 13C NMR spectroscopy. The radiochemical purity of the target compounds was determined by analytical HPLC and exceeded 95%. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis, radiofluorination and first evaluation of (±)-[ 18F]MDL 100907 as serotonin 5-HT2A receptor antagonist for PET

In some psychiatric disorders 5-HT2A receptors play an important role. In order to investigate those in vivo there is an increasing interest in obtaining a metabolically stable, subtype selective and high affinity radioligand for receptor binding studies using positron emission tomography (PET). Combining the excellent in vivo properties of [11C]MDL 100907 for PET imaging of 5-HT2A receptors and the more suitable half-life of fluorine-18, MDL 100907 was radiofluorinated in four steps using 1-(2-bromoethyl)-4-[18F]fluorobenzene as a secondary labelling precursor. The complex reaction required an overall reaction time of 140 min and (±)-[18F]MDL 100907 was obtained with a specific activity of at least 30 GBq/μmol (EOS) and an overall radiochemical yield of 1-2%. In order to verify its binding to 5-HT2A receptors, in vitro rat brain autoradiography was conducted showing the typical distribution of 5-HT 2A receptors and a very low non-specific binding of about 6% in frontal cortex, using ketanserin or spiperone for blocking. Thus, [18F]MDL 100907 appears to be a promising new 5-HT2A PET ligand. Copyright

Processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol"

The present invention provides various processes for the preparation of (R)-±-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol. These processes may be characterized by the following scheme: