1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide

Base Information

• Chemical Name: 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide
• CAS No.: 1429896-46-7
• Molecular Formula: C₂₃H₂₄N₂O₂
• Molecular Weight: 360.456
• Mol file: 1429896-46-7.mol

Synonyms:1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide

Chemical Property of 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide

There total 5 articles about 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide 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: 69.0%

1-methyl-N-(quinolin-8-yl)cyclopentane-1-carboxamide (1429896-60-5) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide (1429896-46-7)

Guidance literature:

1-methyl-N-(quinolin-8-yl)cyclopentane-1-carboxamide; 4-methoxyphenyl magnesium bromide; With N,N,N,N,-tetramethylethylenediamine; zinc dibromide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With iron(III)-acetylacetonate; 1,2-dichloro-2-methylpropane; o-phenylenebis(diphenylphosphine); In tetrahydrofuran; at 20 - 50 ℃; for 36h;

DOI:10.1021/ja402806f

Reference yield:

ethyl cyclopentanecarboxylate (5453-85-0) → 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide (1429896-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 10 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / methanol / 60 °C

2.2: pH 2

3.1: thionyl chloride / 3 h / 85 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: N,N,N,N,-tetramethylethylenediamine; zinc dibromide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: 36 h / 20 - 50 °C

With n-butyllithium; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ja402806f

Reference yield:

ethyl 1-methyl-1-cyclopentanecarboxylate (6553-72-6) → 1-(4-methoxybenzyl)-N-(quinolin-8-yl)cyclopentanecarboxamide (1429896-46-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / methanol / 60 °C

1.2: pH 2

2.1: thionyl chloride / 3 h / 85 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: N,N,N,N,-tetramethylethylenediamine; zinc dibromide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.2: 36 h / 20 - 50 °C

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; triethylamine; sodium hydroxide; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja402806f

upstream raw materials:

ethyl 1-methyl-1-cyclopentanecarboxylate

1-methylcyclopentanecarboxylic acid

1-methylcyclopentanecarbonyl chloride

ethyl cyclopentanecarboxylate

Refernces