trans-Tramadol

Base Information

• Chemical Name: trans-Tramadol
• CAS No.: 152538-36-8
• Molecular Formula: C16H25NO2
• European Community (EC) Number: 604-862-4
• UNII: 7AO28L53FN,45PA5S9V4D
• DSSTox Substance ID: DTXSID401317389
• Nikkaji Number: J354.350A
• Wikidata: Q27266848
• Mol file: 152538-36-8.mol

Synonyms:trans-Tramadol;Tramadol, trans-;152538-36-8;(+/-)-trans-Tramadol;Tramadol, trans-(+)-;UNII-7AO28L53FN;45PA5S9V4D;7AO28L53FN;(1R,2S)-2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXAN-1-OL;(1RS,2SR)-2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol;Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, (1R,2S)-rel-;Tramadol hydrochloride specified impurity A [EP];Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, (1R,2S)-;2148284-56-2;(1R,2S)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexan-1-ol;UNII-45PA5S9V4D;SCHEMBL1593740;DTXSID401317389;27203-92-5 (free base);Q27266848;TRAMADOL HYDROCHLORIDE IMPURITY A [EP IMPURITY];2alpha-[(Dimethylamino)methyl]-1alpha-(3-methoxyphenyl)cyclohexan-1-ol

Chemical Property of trans-Tramadol

Chemical Property:

• Vapor Pressure: 1.02E-06mmHg at 25°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 282

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O
• Isomeric SMILES: CN(C)C[C@@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O

Technology Process of trans-Tramadol

There total 47 articles about trans-Tramadol 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: 98.0%

tramadol hydrochloride (36282-47-0,22204-88-2) → 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)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 0.25h;

Reference yield: 66.0%

rel-(1R,2S)-2-(bromomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol + dimethyl amine (124-40-3) → 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)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1002/adsc.201901533

Reference yield:

2-[(dimethylamino)methyl]cyclohexanone (769092-24-2) + (3-methoxyphenyl)magnesium bromide (36282-40-3) → (±)-(1R,2S)-2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol (2914-77-4,27203-92-5,73806-46-9,123134-25-8,123154-38-1,152538-36-8,181289-58-7,181289-59-8) + 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)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 0.55h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2010.02.078

upstream raw materials:

2-[(dimethylamino)methyl]cyclohexanone

(3-methoxyphenyl)magnesium bromide

C₁₆H₂₅NO₂*C₈H₈O₃

cis-tramadol

Downstream raw materials:

(±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol

(-)-cis-tramadol (R)-(-)-mandelate

(+)-cis-tramadol R-(-)-mandelate

(+)-tramadol*(L)-(+)-mandelic acid

Refernces

• 1、 Mita, Tsuyoshi,Sato, Yoshihiro,Uchiyama, Masashi. "Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)?H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds". . . Retrieved 2020/02/05.
• 2、 Naghdi, Elahe,Fakhari, Ali Reza. "Simultaneous chiral separation of tramadol and methadone in tablets, human urine, and plasma by capillary electrophoresis using maltodextrin as the chiral selector". . p. 1161 - 1168. Retrieved 2018/09/06.