(1S,2S)-1-(4-chloro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

Base Information

• Chemical Name: (1S,2S)-1-(4-chloro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS No.: 169249-10-9
• Molecular Formula: C₁₈H₂₀ClNO
• Molecular Weight: 301.816
• DSSTox Substance ID: DTXSID40456340
• Nikkaji Number: J1.772.129A
• Wikidata: Q82278745
• Mol file: 169249-10-9.mol

Synonyms:CTK4D3239;169249-10-9;DTXSID40456340;(1S)-N-Methyl-1alpha-(3-methoxy-4-chlorophenyl)-1,2,3,4-tetrahydronaphthalene-2beta-amine

Chemical Property of (1S,2S)-1-(4-chloro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 301.1233420
• Heavy Atom Count: 21
• Complexity: 337

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCC2=CC=CC=C2C1C3=CC(=C(C=C3)Cl)OC
• Isomeric SMILES: CN[C@H]1CCC2=CC=CC=C2[C@@H]1C3=CC(=C(C=C3)Cl)OC

Technology Process of (1S,2S)-1-(4-chloro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

There total 9 articles about (1S,2S)-1-(4-chloro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-2-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: 95.0%

C24H23ClN2O5S (1369217-07-1) → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine (169249-10-9)

Guidance literature:

With 4-Methoxybenzenethiol; potassium carbonate; In dimethyl sulfoxide; acetonitrile; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.01.017

Reference yield:

(2S)-methyl [1-(4-chloro-3-methoxyphenyl)-1,2,3,4-tetrahydro-2-naphthalenyl]carbamate → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine (169249-10-9) + cis-(1R,2S)-1-(4-chloro-3-methoxyphenyl)-1,2,3,4-tetrahydro-N-methyl-2-naphthalenamine

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; for 1h; Overall yield = 91 %; Reflux; Inert atmosphere;

Reference yield:

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene → (+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine (169249-10-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(II) bis(trifluoromethanesulfonate); (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) / dichloromethane / 3 h / 32 °C / Inert atmosphere; Molecular sieve

1.2: 1 h / 32 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 4 h / 20 °C / Inert atmosphere

3.1: 4-Methoxybenzenethiol; potassium carbonate / dimethyl sulfoxide; acetonitrile / 5 h / 20 °C / Inert atmosphere

With 4-Methoxybenzenethiol; copper(II) bis(trifluoromethanesulfonate); sodium hydride; (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline); potassium carbonate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.2: Friedel Crafts alkylation;

DOI:10.1016/j.tetasy.2012.01.017

upstream raw materials:

3-phenyl-propionaldehyde

1-chloro-2-methoxy-4-(4-phenyl-but-1-enyl)-benzene

(+)-trans-N-[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-nitro-benzenesulfonamide

C₂₄H₂₃ClN₂O₅S

Downstream raw materials:

{[1-(4-chloro-3-methoxy-phenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methyl-amino}-acetic acid methyl ester

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