R-Dapoxetine

Base Information

• Chemical Name: R-Dapoxetine
• CAS No.: 119357-36-7
• Molecular Formula: C21H23NO
• Molecular Weight: 305.42
• Mol file: 119357-36-7.mol

Synonyms:R-Dapoxetine;ent-Dapoxetine;(alphaR)-N,N-Dimethyl-alpha-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine

Chemical Property of R-Dapoxetine

Chemical Property:

• Boiling Point: 454.4±38.0 °C(Predicted)
• PKA: 8.38±0.50(Predicted)
• PSA: 12.47000
• Density: 1.081±0.06 g/cm3(Predicted)
• LogP: 4.91160

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of R-Dapoxetine

There total 11 articles about R-Dapoxetine 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: 92.0%

tert-butyl (R,E)-(3-(naphthalen-1-yloxy)-1-phenylallyl)carbamate → (R)-N,N-dimethyl-α-[2-(1-naphthyloxy)ethyl]benzylamine (119357-36-7,119356-77-3)

Guidance literature:

tert-butyl (R,E)-(3-(naphthalen-1-yloxy)-1-phenylallyl)carbamate; With palladium 10% on activated carbon; hydrogen; In methanol; dichloromethane; at 20 ℃;

With trifluoroacetic acid; In methanol; dichloromethane; at 20 ℃; for 1h;

With formaldehyd; In methanol; dichloromethane; water; for 16h;

DOI:10.1021/acs.orglett.5b01755

Reference yield: 91.2%

→ (R)-N,N-dimethyl-α-[2-(1-naphthyloxy)ethyl]benzylamine (119357-36-7,119356-77-3)

Guidance literature:

In water; at 90 - 110 ℃; Inert atmosphere;

Reference yield: 79.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-methyl-[3-(naphthalen-1-yloxy)-1-phenyl-propyl]-amine (1202160-36-8,147199-39-1) → (R)-N,N-dimethyl-α-[2-(1-naphthyloxy)ethyl]benzylamine (119357-36-7,119356-77-3)

Guidance literature:

formaldehyd; (R)-methyl-[3-(naphthalen-1-yloxy)-1-phenyl-propyl]-amine; With formic acid; In water; for 8h; Reflux; Inert atmosphere;

With hydrogenchloride; In water; pH=1; Inert atmosphere;

With sodium hydroxide; In water; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jo902176s

upstream raw materials:

formaldehyd

(R)-methyl-[3-(naphthalen-1-yloxy)-1-phenyl-propyl]-amine

α-naphthol

(R)-(-)-3-(dimethylamino)-3-phenyl-1-propanol

Downstream raw materials:

(R)-N,N-dimethyl-α-[2-(1-naphthyloxy)ethyl]benzylamine hydrochloride

Refernces

• 1、 -. "Preparation and detection method of dapoxetine hydrochloride isomer impurities". Paragraph 0013; 0017; 0019-0020. . Retrieved 2020/05/01.
• 2、 Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian. "Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane". supporting information. p. 1042 - 1047. Retrieved 2016/04/19.