(R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine

Base Information

• Chemical Name: (R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine
• CAS No.: 166742-75-2
• Molecular Formula: C10H14N2
• Molecular Weight: 162.23
• DSSTox Substance ID: DTXSID60432868
• Mol file: 166742-75-2.mol

Synonyms:(R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine;166742-75-2;(3R)-N-methyl-1,2,3,4-tetrahydroquinolin-3-amine;(R)-1,2,3,4-tetrahydro-N-methyl-3-quinolinamine;SCHEMBL4798460;DTXSID60432868;IQDMUSPYIULEGD-SECBINFHSA-N;CS-M0364;CS-14265

Chemical Property of (R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine

Chemical Property:

• Boiling Point: 297.3±29.0 °C(Predicted)
• PKA: 9.22±0.20(Predicted)
• PSA: 24.06000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 1.77150
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.115698455
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-N-methyl-1,2,3,4-tetrahydroquinolin-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CC2=CC=CC=C2NC1
• Isomeric SMILES: CN[C@@H]1CC2=CC=CC=C2NC1

Technology Process of (R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine

There total 5 articles about (R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine 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:

methyl (R)-N-(1,2,3,4-Tetrahydro-1-methoxy-2-oxo-3-quinolinyl)-carbamate (166742-73-0) → (R)-1,2,3,4-tetrahydro-N-methyl-3-quinolinamine (166742-75-2)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; for 30h; Yield given; Ambient temperature;

DOI:10.1021/jo970526a

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (R)-1,2,3,4-tetrahydro-N-methyl-3-quinolinamine (166742-75-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 34 g / NaOH / H₂O; tetrahydrofuran / 2 h / 25 °C

2: 22.6 g / Na₂CO₃, EDC / H₂O; CH₂Cl₂ / 22 h / Ambient temperature

3: 19.58 g / PhI(OCOCF₃)2 / trifluoroacetic acid; CH₂Cl₂ / 1 h / 0 °C

4: BH₃*Me₂S / tetrahydrofuran / 30 h / Ambient temperature

With sodium hydroxide; dimethylsulfide borane complex; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; dichloromethane; water; trifluoroacetic acid;

DOI:10.1021/jo970526a

Reference yield:

(R)-N-(methoxycarbonyl)phenylalanine (67401-65-4) → (R)-1,2,3,4-tetrahydro-N-methyl-3-quinolinamine (166742-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 22.6 g / Na₂CO₃, EDC / H₂O; CH₂Cl₂ / 22 h / Ambient temperature

2: 19.58 g / PhI(OCOCF₃)2 / trifluoroacetic acid; CH₂Cl₂ / 1 h / 0 °C

3: BH₃*Me₂S / tetrahydrofuran / 30 h / Ambient temperature

With dimethylsulfide borane complex; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; dichloromethane; water; trifluoroacetic acid;

DOI:10.1021/jo970526a

upstream raw materials:

methyl (R)-N-(1,2,3,4-Tetrahydro-1-methoxy-2-oxo-3-quinolinyl)-carbamate

D-(R)-phenylalanine

(R)-N-(methoxycarbonyl)phenylalanine

(R)-N-methoxy-2-(methoxycarbonylamino)-3-phenylpropanamide

Downstream raw materials:

(R)-methyl-(1,2,3,4-tetrahydro-3-quinolinyl)carbamic acid, phenylmethyl ester