Radafaxine

Base Information

• Chemical Name: Radafaxine
• CAS No.: 192374-14-4
• Molecular Formula: C13H18ClNO2
• Molecular Weight: 255.744
• European Community (EC) Number: 689-763-4
• UNII: Q47741214K
• DSSTox Substance ID: DTXSID501318447
• Nikkaji Number: J1.493.314J
• Wikipedia: Radafaxine
• Wikidata: Q1485208
• NCI Thesaurus Code: C81083
• Pharos Ligand ID: ZH4KDRQ2SYM6
• Metabolomics Workbench ID: 152887
• ChEMBL ID: CHEMBL1172928
• Mol file: 192374-14-4.mol

Synonyms:2-morpholinol, 2-(3-chlorophenyl)-3,5,5-trimethyl-, (2S,3S)-;radafaxine

Chemical Property of Radafaxine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 121-123°C
• Boiling Point: 386.574°C at 760 mmHg
• Flash Point: 187.594°C
• PSA: 41.49000
• Density: 1.144g/cm³
• LogP: 3.40280
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 255.1026065
• Heavy Atom Count: 17
• Complexity: 285

Purity/Quality:

98%Min ^*data from raw suppliers

(S,S)-HydroxyBupropion ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OCC(N1)(C)C)(C2=CC(=CC=C2)Cl)O
• Isomeric SMILES: C[C@H]1[C@@](OCC(N1)(C)C)(C2=CC(=CC=C2)Cl)O
• Recent ClinicalTrials: An 8 Week Study Of Depression In Adults Diagnosed With Major Depressive Disorder
• Recent EU Clinical Trials: A Multicentre, Randomised, Double-Blind, Placebo-Controlled, Parallel-Group, Flexible-Dose Study Evaluating the Efficacy, Safety, and Tolerability of Radafaxine Extended-Release (100-140mg/day) Compared to Placebo in Adult Subjects Diagnosed with Major Depressive Disorder.
• Uses: (S,S) Enantiomer metabolite of Bupropion (B689625), an antidepressant.

Technology Process of Radafaxine

There total 7 articles about Radafaxine 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: 41.0%

2-Amino-2-methyl-1-propanol (124-68-5) + (R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one (291275-46-2) → radafaxine (192374-14-4,233600-52-7)

Guidance literature:

(R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one; With trifluoromethylsulfonic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at -50 - 0 ℃; for 1h;

2-Amino-2-methyl-1-propanol; In dichloromethane; acetonitrile; at -10 - 0 ℃; for 4h;

Reference yield: 32.0%

(S)-3,5,5-trimethylmorpholin-2-one (1231951-61-3) + (3-chlorophenyl)magnesium bromide (36229-42-2) → radafaxine (192374-14-4,233600-52-7)

Guidance literature:

(S)-3,5,5-trimethylmorpholin-2-one; (3-chlorophenyl)magnesium bromide; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %ee;

DOI:10.1021/jm1003232

Reference yield:

(2SR,3SR)-hydroxybupropion (233600-52-7) → radafaxine (192374-14-4,233600-52-7)

Guidance literature:

With hydrogenchloride; Pseudomonas fluorescens p-30 lipase; In water; acetone; at 20 ℃; for 16h; pH=6 - 7; Purification / work up; Resolution of racemate;

upstream raw materials:

2-Amino-2-methyl-1-propanol

Trifluoro-methanesulfonic acid (R)-2-(3-chloro-phenyl)-1-methyl-2-oxo-ethyl ester

3'-chloro-propiophenone

(R)-(+)-1-(3-chlorophenyl)-2-hydroxypropan-1-one

Downstream raw materials:

(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride

(2S,3S)-2-(3-chlorophenyl)-3,4,5,5-tetramethylmorpholin-2-ol

Refernces

• 1、 Lukas, Ronald J.,Muresan, Ana Z.,Damaj, M. Imad,Blough, Bruce E.,Huang, Xiaodong,Navarro, Hernán A.,Mascarella, S. Wayne,Eaton, J. Brek,Marxer-Miller, Syndia K.,Carroll, F. Ivy. "Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: Aids to smoking cessation". experimental part. p. 4731 - 4748. Retrieved 2010/10/03.
• 2、 Fang, Qun K.,Han, Zhengxu,Grover, Paul,Kessler, Donald,Senanayake, Chris H.,Wald, Stephen A.. "Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate". . p. 3659 - 3663. Retrieved 2007/10/03.