192374-14-4

Basic information

• Product Name: (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE
• Synonyms: (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE;2-MORPHOLINOL, 2-(3-CHLOROPHENYL)-3,5,5-TRIMETHYL-, HYDROCHLORIDE, (2S,3S)-;GW 353162A;RADAFAXINE HYDROCHLORIDE;(S,S)-Hydroxy Bupropion;(2S,3S)-2-(3-Chlorophenyl)-3,5,5-triMethyl-2-Morpholinol;(2S-cis)-2-(3-Chlorophenyl)-3,5,5-triMethyl-;Radafaxine
• CAS NO: 192374-14-4
• Molecular Formula: C₁₃H₁₈ClNO₂
• Molecular Weight: 255.74
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 192374-14-4.mol

Chemical Properties

• Melting Point: 121-123°C
• Boiling Point: 386.574°C at 760 mmHg
• Flash Point: 187.594°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE(192374-14-4)
• EPA Substance Registry System: (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE(192374-14-4)

Safety Data

• Hazardous Substances Data: 192374-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE is used as an enantiomer metabolite for the development of chiral drugs. Its specific configuration (S,S) is crucial for the activity, safety, and efficacy of the resulting pharmaceutical products. The compound serves as a key intermediate in the synthesis of enantiomerically pure drugs, particularly in the field of antidepressants, such as Bupropion (B689625).
Used in Chemical Research:
As a chiral compound with a unique structure, (2S,3S)-2-(3-CHLORO-PHENYL)-3,5,5-TRIMETHYL-MORPHOLIN-2-OL HYDROCHLORIDE can be used in chemical research for the development of novel chiral catalysts, ligands, and other chiral auxiliaries. Its specific stereochemistry and functional groups make it a valuable building block for the synthesis of complex organic molecules with potential applications in various industries.
Used in Analytical Chemistry:
The compound's distinct enantiomeric configuration and chemical properties make it suitable for use in analytical chemistry, particularly in the development of chiral stationary phases for high-performance liquid chromatography (HPLC) and other separation techniques. These techniques are essential for the analysis and purification of enantiomers in pharmaceuticals, agrochemicals, and other chiral compounds.

InChI:InChI=1/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3

Upstream product

• 1231951-61-3 (S)-3,5,5-trimethylmorpholin-2-one 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 291275-46-2 (R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one 
• 233600-52-7 (2SR,3SR)-hydroxybupropion 
• 291275-45-1 (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane 
• 34841-35-5 3'-chloro-propiophenone 
• 291275-48-4 Trifluoro-methanesulfonic acid (R)-2-(3-chloro-phenyl)-1-methyl-2-oxo-ethyl ester 

Downstream Products

• 106083-71-0 (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride 
• 1231951-92-0 (2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol 

Relevant articles and documents

HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: Aids to smoking cessation

To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropions possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,3S)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3′,4′-dichlorophenyl [(±)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3′-fluorophenyl, 3′-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of α4β2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,3S)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of α4β2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.

ENZYME-CATALYZED DYNAMIC KINETIC RESOLUTION PROCESS FOR PREPARING (+)-(2S, 3S)-2-(3-CHLOROPHENYL)-3,5,5-TRIMETHYL-2-MORPHOLINOL, SALTS, AND SOLVATES THEREOF

A process for preparing (+)-(2S, 3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol, pharmaceutically acceptable salts and solvates thereof such as the (+)-(2S, 3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride salt via enzyme-cataly

Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

A stereospecific method for the synthesis of enantiopure α-aminoketone from its corresponding α-hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupro