Hydroxy Bupropion

Base Information

• Chemical Name: Hydroxy Bupropion
• CAS No.: 357399-43-0
• Molecular Formula: C13H18ClNO2
• Molecular Weight: 255.744
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90431622
• Nikkaji Number: J2.509.039J
• ChEMBL ID: CHEMBL4561343
• Mol file: 357399-43-0.mol

Synonyms:Hydroxy Bupropion;357399-43-0;Bupropion morpholinol;2-(3-CHLOROPHENYL)-3,5,5-TRIMETHYLMORPHOLIN-2-OL;2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol;2-Hydroxy-2-(3'-chlorophenyl)-3,5,5-trimethylmorpholine;BUPROPIONMORPHOLINOL;Oprea1_654095;SCHEMBL2599138;CHEMBL4561343;DTXSID90431622;RCOBKSKAZMVBHT-UHFFFAOYSA-N;AKOS025149627;AS-6162;CS-O-06114;FT-0669436;FT-0669437;FT-0669438;2-(3-Chlorophenyl)-3,5,5-trimethylmorpholine-2-ol;2-Hydroxy-2-(3?-chlorophenyl)-3,5,5-trimethylmorpholine

Chemical Property of Hydroxy Bupropion

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 121-123°C
• Refractive Index: 1.523
• Boiling Point: 386.574 °C at 760 mmHg
• Flash Point: 187.594 °C
• PSA: 41.49000
• Density: 1.144 g/cm³
• LogP: 2.60080
• Storage Temp.: -20°C Freezer
• 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:

99% ^*data from raw suppliers

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
• Uses: A metabolite of Bupropion, an antidepressant. The compound exists mainly as cyclic acetal (2-hydroxy-2-(3’-chlorophenyl)-355-trimethylmorpholine). See US Pat. # 634.2496 A metabolite of Bupropion, an antidepressant. The compound exists mainly as cyclic acetal (2-hydroxy-2-(3’-chlorophenyl)-355-trimethylmorpholine). See US Pat. # 6342496.

Technology Process of Hydroxy Bupropion

There total 6 articles about Hydroxy Bupropion 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: 90.0%

2-bromo-3'-chloropropiophenone (34911-51-8) + 2-Amino-2-methyl-1-propanol (124-68-5) → (2R,3R)-2-(-3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol (357399-43-0,233600-52-7)

Guidance literature:

In ethyl acetate; acetonitrile;

Reference yield:

C35H37ClN2O8 (913728-80-0) → (2R,3R)-2-(-3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol (357399-43-0,233600-52-7) + 5-(3-chlorophenyl)-3-(2-hydroxy-1,1-dimethylethyl)-4-methyloxazolin-2-one + Naltrexone (16590-41-3)

Guidance literature:

With phosphate buffer; Hank's buffer; In water; at 32 ℃; pH=7.4; Kinetics;

DOI:10.1016/j.bmc.2006.06.018

Reference yield:

3'-chloro-propiophenone (34841-35-5) → (2R,3R)-2-(-3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol (357399-43-0,233600-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / CH₂Cl₂ / cooling

2: 17.3 g / 1-methyl-pyrrolidin-2-one / 0.83 h / 50 - 60 °C

With bromine; In 1-methyl-pyrrolidin-2-one; dichloromethane;

DOI:10.1016/j.bmc.2006.06.018

upstream raw materials:

C₃₅H₃₇ClN₂O₈

C₃₅H₃₉ClN₂O₈

2-bromo-3'-chloropropiophenone

2-Amino-2-methyl-1-propanol

Downstream raw materials:

5-(3-chlorophenyl)-3-[2-(chlorocarbonyloxy)-1,1-dimethylethyl]-4-methyloxazolin-2-one

Refernces

• 1、 -. "Enhancing transdermal delivery of opiod antagonists and agonistis using codrugs links to bupropion or hydroxybupropion". Page/Page column 7. . Retrieved 2009/01/24.
• 2、 -. "Pharmaceutically active morpholinol". . . Retrieved 2008/06/13.