8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline

Base Information

• Chemical Name: 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline
• CAS No.: 1385015-54-2
• Molecular Formula: C₂₇H₂₆FN₃O
• Molecular Weight: 427.521
• Mol file: 1385015-54-2.mol

Synonyms:

Chemical Property of 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline

There total 6 articles about 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline 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: 32.0%

5-(4-fluorophenyl)nicotinaldehyde (381684-96-4) + 2-methoxy-8-(piperidin-4-yl)quinoline, trifluroacetate (1385015-39-3) → 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline (1385015-54-2)

Guidance literature:

With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1515/znb-2012-0312

Reference yield: 32.0%

→ 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline (1385015-54-2)

Guidance literature:

With triethylamine; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 0.166667h;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃;

Reference yield:

tert-butyl 4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → 8-(4-((5-(4-fluorophenyl)pyridin-3-yl)methyl)piperazin-1-yl)-2-methoxyquinoline (1385015-54-2)

Guidance literature:

Multi-step reaction with 4 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 14 h / 80 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 20 °C

3: dichloromethane / 6 h / 0 - 20 °C

4: sodium tris(acetoxy)borohydride; triethylamine / dichloromethane / 0 - 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1515/znb-2012-0312

upstream raw materials:

5-(4-fluorophenyl)nicotinaldehyde

2-methoxy-8-(piperidin-4-yl)quinoline, trifluroacetate

tert-butyl 4-(2-methoxyquinolin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate

tert-butyl 4-(2-methoxyquinolin-8-yl)piperidine-1-carboxylate

Refernces

• 1、 Ullah, Nisar,Al-Shaheri, Ali Ahmed Qaid. "Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)". experimental part. p. 253 - 262. Retrieved 2012/06/30.