N,N-Diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide

Base Information

• Chemical Name: N,N-Diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide
• CAS No.: 105279-00-3
• Molecular Formula: C₂₃H₂₆N₂O
• Molecular Weight: 346.472
• DSSTox Substance ID: DTXSID00909408
• Nikkaji Number: J438.806B,J438.807K
• Mol file: 105279-00-3.mol

Synonyms:DEMPQP;N,N-diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide;N,N-diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide, (+)-isomer

Chemical Property of N,N-Diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide

Chemical Property:

• Vapor Pressure: 4.85E-11mmHg at 25°C
• Boiling Point: 523.2°Cat760mmHg
• Flash Point: 270.2°C
• PSA: 33.20000
• Density: 1.087g/cm³
• LogP: 4.94880
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 346.204513457
• Heavy Atom Count: 26
• Complexity: 442

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C(C)CC1=CC(=NC2=CC=CC=C21)C3=CC=CC=C3

Technology Process of N,N-Diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide

There total 4 articles about N,N-Diethyl-alpha-methyl-2-phenyl-4-quinolinepropanamide 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:

N,N-diethyl-2-methylpent-4-ynamide (1616976-79-4) → (R)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105279-00-3) + (S)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105306-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) chloride; silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 17 h / 100 °C / Inert atmosphere

2: Lux, 12, O₂/A₃, 50:50 / Resolution of racemate

With silver trifluoromethanesulfonate; copper(l) chloride; In 1,2-dichloro-ethane;

DOI:10.1021/jm5007947

Reference yield:

(+/-)-2-methylpent-4-ynoic acid (74064-82-7) → (R)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105279-00-3) + (S)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105306-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 2 h / 20 °C

2: copper(l) chloride; silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 17 h / 100 °C / Inert atmosphere

3: Lux, 12, O₂/A₃, 50:50 / Resolution of racemate

With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; copper(l) chloride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm5007947

Reference yield:

N,N-diethylpropanamide (1114-51-8) → (R)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105279-00-3) + (S)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide (105306-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; toluene; tetrahydrofuran / -75 - 20 °C / Inert atmosphere

2: copper(l) chloride; silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 17 h / 100 °C / Inert atmosphere

3: Lux, 12, O₂/A₃, 50:50 / Resolution of racemate

With n-butyllithium; silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; copper(l) chloride; In tetrahydrofuran; hexane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jm5007947

upstream raw materials:

N,N-diethyl-2-methylpent-4-ynamide

(+/-)-2-methylpent-4-ynoic acid

N,N-diethylpropanamide

Refernces