(-)-Tramadol

Base Information

• Chemical Name: (-)-Tramadol
• CAS No.: 123134-25-8
• Deprecated CAS: 46941-76-8
• Molecular Formula: C₁₆H₂₅NO₂
• Molecular Weight: 263.38
• UNII: 26J30IC20Q
• DSSTox Substance ID: DTXSID601313414
• Nikkaji Number: J238.351I
• Wikidata: Q27145506
• ChEMBL ID: CHEMBL4059722
• Mol file: 123134-25-8.mol

Synonyms:(-)-Tramadol;123134-25-8;(s,s)-tramadol;(-)-(S,S)-trans-Tramadol;(1S,2S)-2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXAN-1-OL;Tramadol, (-)-;CHEMBL4059722;26J30IC20Q;(-)-trans-2-(Dimethylaminomethyl)-1-(m-methoxyphenyl)cyclohexanol;(1S,2S)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol;E 381;Cyclohexanol, 2-(dimethylaminomethyl)-1-(m-methoxyphenyl)-, (-)-(E)-;Cyclohexanol, 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-, (1S,2S)-;(1s,2s)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol;(-)-trans tramadol;SCHEMBL730723;UNII-26J30IC20Q;(-)-(S,S)-TRAMADOL;CHEBI:75731;DTXSID601313414;(-)-2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXANOL;AC-795;BDBM50248249;STK623739;AKOS022060898;SBI-0206831.P001;AB01563069_01;BRD-K51033547-003-01-8;Q27145506;(1S, 2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol;(1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol;(1s,2s)-2-[(dimethyl-amino)-methyl]-1-(3-methoxyphenyl)-cyclohexanol;CYCLOHEXANOL, 2-((DIMETHYLAMINO)METHYL)-1-(3-METHOXYPHENYL)-, (1S-CIS)-;F1U

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Chemical Property of (-)-Tramadol

Chemical Property:

• Boiling Point: 388.1°Cat760mmHg
• Flash Point: 188.5°C
• PSA: 32.70000
• Density: 1.047g/cm³
• LogP: 2.63460
• Storage Temp.: Refrigerator
• 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:

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
• Uses: An analgesic.

Technology Process of (-)-Tramadol

There total 34 articles about (-)-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:

cis-tramadol

1-(Trimethylsilyloxy)cyclohexene

(3-methoxyphenyl)magnesium bromide

methyl trifluoromethanesulfonate

Downstream raw materials:

(1R,2R)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol (S)-naproxen salt

(1S,2S)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol (S)-naproxen salt

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

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

Refernces

• 1、 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.
• 2、 Taheri, Mohammadreza,Fotovati, Mohsen,Hosseini, Seyed-Kiumars,Ghassempour, Alireza. "Optimization of throughput in semipreparative chiral liquid chromatography using stacked injection". . p. 579 - 588. Retrieved 2017.
• 3、 Monos, Timothy M.,Jaworski, Jonathan N.,Stephens, John C.,Jamison, Timothy F.. "Continuous-Flow Synthesis of Tramadol from Cyclohexanone". supporting information. p. 1888 - 1893. Retrieved 2020/11/24.