(1R,4R)-Sertraline HCl

Base Information

• Chemical Name: (1R,4R)-Sertraline HCl
• CAS No.: 79617-98-4
• Molecular Formula: C17H18Cl3N
• Molecular Weight: 306.235
• Mol file: 79617-98-4.mol

Synonyms:(1R,4R)-Sertraline HCl;(R,R)-Sertraline;Sertindole-d4

Chemical Property of (1R,4R)-Sertraline HCl

Chemical Property:

• Melting Point: 243-245 °C
• Boiling Point: 416.3±45.0 °C(Predicted)
• PKA: 9.47±0.40(Predicted)
• PSA: 12.03000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 5.57050
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

Sertindole-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (rac,rac)-4-Sertraline acts as a selective serotonin reuptake inhibitor that displays minor antifungal activity as well. (R,R)-Sertraline acts as a selective serotonin reuptake inhibitor that displays minor antifungal activity as well.

Technology Process of (1R,4R)-Sertraline HCl

There total 20 articles about (1R,4R)-Sertraline HCl 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:

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine (79560-20-6) → (1R,4R)-sertraline (79617-98-4) + trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79951-46-5) + Sertraline (79617-96-2)

Guidance literature:

With R,S-[Ir(1,5-cyclooctadiene)(PPh₂(C₉H₁₀)(C₃H₃NO-i-Bu))] tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen; at 20 ℃; for 12h; under 15201 Torr; optical yield given as %ee; enantioselective reaction;

Reference yield:

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine (79560-20-6) → (1R,4R)-sertraline (79617-98-4) + trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (91797-60-3) + trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79951-46-5) + Sertraline (79617-96-2)

Guidance literature:

With C₃₂H₁₂BF₂₄^(1-)*C₃₆H₄₄IrNOP⁽¹⁺⁾; hydrogen; at 20 ℃; for 12h; under 15201 Torr; optical yield given as %ee; enantioselective reaction;

Reference yield:

(4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine (261776-41-4) → (1R,4R)-sertraline (79617-98-4) + trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79951-46-5) + (4R)-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone (155748-61-1,79836-44-5) + (4S)-4-(3,4-dichlorophenyl)-1-tetralone (124379-29-9,79836-44-5)

Guidance literature:

With (R,R)-(ethylenebis(tetrahydroindenyl))TiF₂; phenylsilane; In tetrahydrofuran; at 20 ℃; for 5h; Title compound not separated from byproducts.;

DOI:10.1021/jo991328h

upstream raw materials:

cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine

(4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

3,4-dichlorobenzophenone

Downstream raw materials:

(4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine

Sertraline

C₉H₉NO₂*C₁₇H₁₇Cl₂N

Refernces

• 1、 -. "RACEMISATION PROCESS FOR OBTAINING (1S,4S) N-METHYL-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-1-NAPHTHALENEAMINE (SERTRALINE)". Page/Page column 14. . Retrieved 2009/04/25.
• 2、 -. "Racemisation process". Page/Page column 14-15. . Retrieved 2008/12/07.