3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol

Base Information

• Chemical Name: 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
• CAS No.: 144830-15-9
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.353
• Hs Code.: 9999999999
• UNII: F4EMT8B1YU
• Nikkaji Number: J434.998I
• Mol file: 144830-15-9.mol

Synonyms:(-)-O-Desmethyl Tramadol;144830-15-9;(-)-O-Demethyltramadol;(-)-O-Desmethyltramadol;F4EMT8B1YU;Desmetramadol, cis-(-)-;Desmetramadol, S,S-(-)-;3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol;UNII-F4EMT8B1YU;3-((1S,2S)-2-((Dimethylamino)methyl)-1-hydroxycyclohexyl)phenol;Phenol, 3-((1S,2S)-2-((dimethylamino)methyl)-1-hydroxycyclohexyl)-;Phenol, 3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)-, (1S-cis)-;SCHEMBL4396389

Chemical Property of 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol

Chemical Property:

• Melting Point: 141-142°C
• Boiling Point: 403.3±25.0 °C(Predicted)
• PKA: 10.00±0.10(Predicted)
• PSA: 43.70000
• Density: 1.104±0.06 g/cm3(Predicted)
• LogP: 3.13360
• Storage Temp.: -20°C Freezer
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.172878976
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

O-Desmethyltramadol hydrochloride analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)O)O
• Isomeric SMILES: CN(C)C[C@@H]1CCCC[C@]1(C2=CC(=CC=C2)O)O
• Uses: A optically active metabolite of Tramadol.

Technology Process of 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol

There total 4 articles about 3-[(1S,2S)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol 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: 80.0%

cis-tramadol (27203-92-5,2914-77-4,73806-46-9,123134-25-8,123154-38-1,36282-47-0,152538-36-8,181289-58-7,181289-59-8) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; for 23h; Cooling with ice; Inert atmosphere; Reflux;

Reference yield:

tramadol (2914-77-4,152538-36-8,181289-58-7,181289-59-8) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 195 - 200 ℃; for 28h; Inert atmosphere;

Reference yield:

tramadol hydrochloride (36282-47-0,22204-88-2) → (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol (73986-53-5,80456-81-1,144830-14-8,144830-15-9) + (±)-cis-2-[(methylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol (147762-57-0,75377-45-6)

Guidance literature:

With titanium dioxide P-25; water; at 25 ℃; for 0.25h; Kinetics; Photolysis;

DOI:10.1016/j.apcata.2016.02.005

upstream raw materials:

tramadol hydrochloride

cis-tramadol

tramadol

Downstream raw materials:

3-<2-(e)-Dimethylaminomethyl-1(a)-hydroxycylohexyl>-phenyl-β-D-glucopyranuronsaeure

(+)-O-Demethyltramadol

Refernces

• 1、 Antonopoulou, Maria,Konstantinou, Ioannis. "Photocatalytic degradation and mineralization of tramadol pharmaceutical in aqueous TiO2 suspensions: Evaluation of kinetics, mechanisms and ecotoxicity". . p. 136 - 143. Retrieved 2016/02/26.