4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline

Base Information

• Chemical Name: 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline
• CAS No.: 104465-71-6
• Molecular Formula: C₂₂H₂₆N₂O
• Molecular Weight: 334.461
• Mol file: 104465-71-6.mol

Synonyms:

Chemical Property of 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline

There total 7 articles about 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline 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: 98.0%

1,2,4-Trimethyl-3-[methyl-(1-phenyl-ethyl)-carbamoyl]-quinolinium; iodide (118743-94-5) → 4S-3--1,2,4-trimethyl-1,4-dihydroquinoline (104465-70-5,104465-71-6,118609-08-8,134623-72-6,134623-73-7)

Guidance literature:

With 4S-3--2,4-dimethyl-1-propyl-1,4-dihydropyridine; In methanol; for 14h; Mechanism; Ambient temperature; further solvent;

DOI:10.1016/S0040-4039(00)82087-0

Reference yield:

1,2,4-Trimethyl-3-[methyl-((R)-1-phenyl-ethyl)-carbamoyl]-quinolinium; iodide (104785-63-9) → (4R)-3--1,2,4-trimethyl-1,4-dihydroquinoline (104465-70-5) + 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline (104465-71-6)

Guidance literature:

With 1-propyl-1,4-dihydronicotinamide; In methanol; for 14h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature; Na₂S₂O₄, borate buffer;

DOI:10.1016/S0040-4020(01)87503-7

Reference yield:

2,4-dimethylquinoline 3-carboxylic acid (104785-55-9) → 4S,11R-3-(N-methyl-N-α-methylbenzyl)carbamoyl-1,2,4-trimethyl-1,4-dihydroquinoline (104465-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) cyanuric chloride; 2.) Et₃N / 1.) acetone, Rt, 4 h; 2.) acetone, Rt, 3 h

2: chromatographic separation of the C-9 diastereomers

3: 1-propyl-1,4-dihydronicotinamide (PNAH) / methanol / 14 h / Ambient temperature; Na₂S₂O₄, borate buffer

With 1,3,5-trichloro-2,4,6-triazine; 1-propyl-1,4-dihydronicotinamide; triethylamine; In methanol;

DOI:10.1016/S0040-4020(01)87503-7

upstream raw materials:

1,2,4-Trimethyl-3-[methyl-(1-phenyl-ethyl)-carbamoyl]-quinolinium; iodide

1,2,4-Trimethyl-3-[methyl-((R)-1-phenyl-ethyl)-carbamoyl]-quinolinium; iodide

2,4-dimethylquinoline 3-carboxylic acid

2-aminoacetophenone

Downstream raw materials:

3-(N-Methyl-N-α-methylbenzylcarbamoyl)-1,2,4-trimethylquinolinium

3--1,2,4-trimethylquinolinium

3--1,2,4-trimethylquinolinium