biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester

Base Information

• Chemical Name: biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester
• CAS No.: 864760-28-1
• Molecular Formula: C₂₉H₃₁N₃O₄
• Molecular Weight: 485.583
• Mol file: 864760-28-1.mol

Synonyms:biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester

Chemical Property of biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Des-4''(methylpiperidine-4-carboxamide)-4''-formyl Revefenacin is an impurity of Revefenacin (R279600). Revefenacin is a pharmaceutical drug for the treatment of chronic obstructive pulmonary diseases.

Technology Process of biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester

There total 12 articles about biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester 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%

biphenyl-2-ylcarbamic acid 1-[2-(methylamino)ethyl]piperidin-4-yl ester (743460-48-2) + 4-Carboxybenzaldehyde (619-66-9) → biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester (864760-28-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 16h;

Reference yield: 90.0%

biphenyl-2-ylcarbamic acid 1-[2-(methylamino)ethyl]piperidin-4-yl ester (743460-48-2) + 4-formylbenzoyl chloride (16173-52-7) → biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester (864760-28-1)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 0.333333h; Reagent/catalyst; Solvent;

Reference yield:

[1,1'-biphenyl]-2-yl-isocyanate (17337-13-2) → biphenyl-2-yl-carbamic acid 1-{2-[(4-formylbenzoyl)methylamino]ethyl}piperidin-4-yl ester (864760-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 12 h / 70 °C

1.2: 12 h / 20 - 40 °C / Inert atmosphere

1.3: pH 12

2.1: 2-methyltetrahydrofuran / 3 - 30 °C

2.2: 7 - 20 °C

2.3: 0.33 h / 20 °C

3.1: hydrogen / palladium 10% on activated carbon / 2-methyltetrahydrofuran; methanol / 3.02 h / 760.05 Torr / Sealed tube

4.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / 2-methyltetrahydrofuran / 20 °C

4.2: 0.17 h

With hydrogen; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; palladium 10% on activated carbon; In 2-methyltetrahydrofuran; methanol;

upstream raw materials:

biphenyl-2-ylcarbamic acid 1-[2-(methylamino)ethyl]piperidin-4-yl ester

4-Carboxybenzaldehyde

1-benzyl-4-hydroxypiperidine

[1,1'-biphenyl]-2-yl-isocyanate

Refernces

• 1、 -. "Preparation methods of revefenacin intermediate and revefenacin". Paragraph 0073; 0078-0079. . Retrieved 2021/05/26.
• 2、 -. "PROCESS FOR PREPARING A BIPHENYL-2-YLCARBAMIC ACID". Page/Page column 11. . Retrieved 2012/02/01.