rac trans Sertraline

Base Information

• Chemical Name: rac trans Sertraline
• CAS No.: 79836-45-6
• Molecular Formula: C17H17 Cl2 N
• Molecular Weight: 306.235
• Mol file: 79836-45-6.mol

Synonyms:1-Naphthalenamine,4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, trans-(?à)-; 1-Naphthalenamine,4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, trans-

Chemical Property of rac trans Sertraline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.621
• Boiling Point: 416.33°C at 760 mmHg
• PKA: 9.47±0.40(Predicted)
• Flash Point: 205.589°C
• PSA: 12.03000
• Density: 1.255g/cm³
• LogP: 5.57050
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dichloromethane (Sparingly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

rac-trans-Sertraline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Rac-trans-Sertraline is used for the treatment of menopause and mood, anxiety, and cognitive disorders. They block uptake of dopamine and norepinephrine. rac-trans-Sertraline (Sertraline EP Impurity A) is used for the treatment of menopause and mood, anxiety, and cognitive disorders. They block uptake of dopamine and norepinephrine.

Technology Process of rac trans Sertraline

There total 11 articles about rac trans Sertraline 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-methyl-N-benzyl-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine → cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine (79617-95-1) + trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79836-45-6)

Guidance literature:

N-methyl-N-benzyl-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine; With hydrogenchloride; palladium 10% on activated carbon; In ethanol; at 20 ℃; for 5h; under 2250230 Torr;

With sodium hydroxide; In water; toluene; for 0.5h;

Reference yield:

(1S*,4R*)-N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-formamide → trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79836-45-6)

Guidance literature:

(1S*,4R*)-N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-formamide; With borane-THF; In tetrahydrofuran; at 20 - 80 ℃;

With hydrogenchloride; In water; at 80 - 90 ℃; for 9h;

With potassium carbonate; In water;

Reference yield:

3,4-dichlorobenzophenone (6284-79-3) → trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (79836-45-6)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium tert-butoxide / 2-methyl-propan-2-ol / 16 h / Heating

2: 50 percent / 48percent aq. HBr / acetic acid / 36 h / Heating

3: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr / Ambient temperature

4: SOCl₂ / toluene / 1.25 h

5: AlCl₃ / CS₂ / 16 h / Ambient temperature

6: TiCl₄ / toluene / 17 h / Ambient temperature

7: sodium borohydride / methanol / 1.5 h / Ambient temperature

With sodium tetrahydroborate; aluminium trichloride; thionyl chloride; potassium tert-butylate; hydrogen bromide; hydrogen; titanium tetrachloride; palladium on activated charcoal; In methanol; carbon disulfide; acetic acid; ethyl acetate; toluene; tert-butyl alcohol;

DOI:10.1021/jm00377a021

upstream raw materials:

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

3,4-dichlorobenzophenone

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

4-(3,4-dichlorophenyl)-4-phenylbutanoic acid

Downstream raw materials:

trans-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride

(1S,4R)-sertraline-(S)-mandelate

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

trans-(1R,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Refernces

• 1、 Taber, Geraldine P.,Pfisterer, David M.,Colberg, Juan C.. "A new and simplified process for preparing N-[4-(3,4-dichlorophenyl)-3,4- dihydro-1(2H)-naphthalenylidene]methanamine and a telescoped process for the synthesis of (1S-cis)-4-(3,4-dichlorophenol)-1,2,3,4-tetrahydro-N-methyl-1- naphthalenamine mandelate: Key intermediates in the synthesis of sertraline hydrochloride". . p. 385 - 388. Retrieved 2013/09/05.
• 2、 Welch, Willard M.,Kraska, Allen R.,Sarges, Reinhard,Koe, B. Kenneth. "Nontricyclic Antidepressant Agents Derived from cis- and trans-1-Amino-4-aryltetralins". . p. 1508 - 1515. Retrieved 2007/10/02.