(R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide

Base Information

• Chemical Name: (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide
• CAS No.: 898533-09-0
• Molecular Formula: C₃₃H₄₀N₄O₃
• Molecular Weight: 540.706
• Mol file: 898533-09-0.mol

Synonyms:(R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide

Chemical Property of (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide

There total 8 articles about (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide 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: 40.0%

(R)-(+)-N-(4-bromobutyl)-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide + 1-(3-methylphenyl)-piperazine dihydrochloride (13078-13-2,178928-62-6) → (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide (898533-09-0)

Guidance literature:

With triethylamine; In acetonitrile; for 12h; Inert atmosphere; Reflux;

DOI:10.1021/jm501119j

Reference yield: 40.0%

→ (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide (898533-09-0)

Guidance literature:

Reference yield:

1,2,3,4-tetrahydroquinoline-2-carboxylic acid (46185-24-4) → (R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1-(benzyloxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxamide (898533-09-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 16 h / 0 - 20 °C

2.1: α-chymotrypsin / aq. phosphate buffer / 20 °C / pH 7.5 / Enzymatic reaction

3.1: sodium hydrogencarbonate / water / 2 h / 20 °C

4.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 12 h / 20 °C

5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2 h / 20 °C

6.1: triethylamine / acetonitrile / 12 h / Inert atmosphere; Reflux

With thionyl chloride; carbon tetrabromide; α-chymotrypsin; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In aq. phosphate buffer; dichloromethane; water; acetonitrile;

DOI:10.1021/jm501119j

upstream raw materials:

quinoline-2-carboxylic acid

1,2,3,4-tetrahydroquinoline-2-carboxylic acid

1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester

(2R)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Downstream raw materials:

(R)-(+)-N-[4-[4-(m-tolyl)piperazin-1-yl]butyl]-1,2,3,4-tetrahydroquinoline-2-carboxamide