Tametraline

Base Information

• Chemical Name: Tametraline
• CAS No.: 52795-02-5
• Molecular Formula: C17H19N
• Molecular Weight: 237.345
• Hs Code.: 2921499090
• UNII: 440C8K5Y5K
• DSSTox Substance ID: DTXSID90200774
• Nikkaji Number: J238.286E
• Wikipedia: Tametraline
• Wikidata: Q29638093
• NCI Thesaurus Code: C152501
• ChEMBL ID: CHEMBL38120
• Mol file: 52795-02-5.mol

Synonyms:TAMETRALINE;52795-02-5;Tametraline [INN];CP-24441;(1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine;CHEMBL38120;UNII-440C8K5Y5K;CP-24,441;440C8K5Y5K;CP 24441;SCHEMBL1237908;BDBM82219;DTXSID90200774;CAS_52760-47-1;Q29638093

Chemical Property of Tametraline

Chemical Property:

• Vapor Pressure: 1.45E-05mmHg at 25°C
• Boiling Point: 366.5°Cat760mmHg
• Flash Point: 183.7°C
• PSA: 12.03000
• Density: 1.06g/cm³
• LogP: 4.26370
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 237.151749610
• Heavy Atom Count: 18
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

Tametraline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCC(C2=CC=CC=C12)C3=CC=CC=C3
• Isomeric SMILES: CN[C@@H]1CC[C@H](C2=CC=CC=C12)C3=CC=CC=C3
• Uses: Antidepressant. Tametraline is a novel GABAA receptor blocker and a reactant in the preparation of (+)-sertraline and (-)-CP-52002.

Technology Process of Tametraline

There total 11 articles about Tametraline 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: 85.0%

methyl(4-phenyl-3,4-dihydro-2H-naphthalen-1-ylidene)amine (261776-39-0) → (4S)-3,4-dihydro-4-phenyl-1(2H)-naphthalenone (91797-70-5) + CP 24441 (52795-02-5) + (1R,4R)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine

Guidance literature:

With (R,R)-(ethylenebis(tetrahydroindenyl))TiF₂; phenylsilane; In tetrahydrofuran; at 13 ℃; for 15h;

DOI:10.1021/jo991328h

Reference yield:

4-phenyl-3,4-dihydronaphthalen-1(2H)-one (14578-68-8) → CP 24441 (52795-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / TiCl₄ / diethyl ether / -35 - 20 °C

2: (R,R)-(ethylenebis(tetrahydroindenyl))TiF₂; PhSiH₃ / tetrahydrofuran / 15 h / 13 °C

With (R,R)-(ethylenebis(tetrahydroindenyl))TiF₂; phenylsilane; titanium tetrachloride; In tetrahydrofuran; diethyl ether; 1: Condensation / 2: kinetic resolution;

DOI:10.1021/jo991328h

Reference yield:

1-Methylimino-4-phenyl-1,2,3,4-tetrahydronaphthalin (52789-19-2) → CP 24441 (52795-02-5)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1021/jo00897a008

upstream raw materials:

1-Methylimino-4-phenyl-1,2,3,4-tetrahydronaphthalin

4-phenyl-3,4-dihydronaphthalen-1(2H)-one

(+/-)-cis-1-Methylamino-4-phenyltetralin

methyl(4-phenyl-3,4-dihydro-2H-naphthalen-1-ylidene)amine

Downstream raw materials:

1-Methylimino-4-phenyl-1,2,3,4-tetrahydronaphthalin

Ethyl-[4-phenyl-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-amine

Isopropyl-[4-phenyl-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-amine

trans-dl-N-methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthylamine

Refernces

• 1、 Yun, Jaesook,Buchwald, Stephen L.. "Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones". . p. 767 - 774. Retrieved 2007/10/03.