(s)-n-Methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine

Base Information

• Chemical Name: (s)-n-Methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine
• CAS No.: 112066-66-7
• Molecular Formula: C₁₇H₂₁NO₂
• Molecular Weight: 271.359
• UNII: D6W2AVH65E
• Nikkaji Number: J259.977E
• Wikidata: Q27276184
• ChEMBL ID: CHEMBL1409777
• Mol file: 112066-66-7.mol

Synonyms:Nisoxetine, (S)-;Nisoxetine, (-)-;UNII-D6W2AVH65E;D6W2AVH65E;(s)-n-methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine;112066-66-7;Benzenepropanamine, gamma-(2-methoxyphenoxy)-N-methyl-, (S)-;Benzenepropanamine, gamma-(2-methoxyphenoxy)-N-methyl-, (gammaS)-;(S)-Nisoxetine;(-)-nisoxetine;Tocris-1025;Lopac-N-151;SCHEMBL3897550;CHEMBL1409777;(3S)-3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine;NCGC00015715-01;NCGC00015715-02;NCGC00016883-01;NCGC00024945-01;CAS-57754-86-6;Q27276184;BENZENEPROPANAMINE, .GAMMA.-(2-METHOXYPHENOXY)-N-METHYL-, (S)-;BENZENEPROPANAMINE, .GAMMA.-(2-METHOXYPHENOXY)-N-METHYL-, (.GAMMA.S)-;41U

Chemical Property of (s)-n-Methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 271.157228913
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNCCC(C1=CC=CC=C1)OC2=CC=CC=C2OC
• Isomeric SMILES: CNCC[C@@H](C1=CC=CC=C1)OC2=CC=CC=C2OC

Technology Process of (s)-n-Methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine

There total 20 articles about (s)-n-Methyl-3-(2-methoxyphenoxy)-3-phenylpropylamine 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: 80.0%

(S)-N-(ethoxycarbonyl)-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine (191733-29-6) → (S)-N-methyl-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine (112066-66-7,57226-61-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0957-4166(02)00537-2

Reference yield: 50.0%

-(-)-1-chloro-3-phenyl-3-(2-methoxyphenoxy)propane (114446-52-5) + methylamine (74-89-5) → (S)-N-methyl-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine (112066-66-7,57226-61-6)

Guidance literature:

In ethanol; at 130 ℃; for 6h; Heating;

DOI:10.1039/b000846j

Reference yield:

[(S)-3-(2-Methoxy-phenoxy)-3-phenyl-propyl]-carbamic acid methyl ester → (S)-N-methyl-3-(2-methoxyphenoxy)-3-phenyl-1-propanamine (112066-66-7,57226-61-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; enantioselective reaction; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.6b02393

upstream raw materials:

2-Chloroanisole

(S)-N-methyl-3-amino-1-phenyl-1-propanol

-(-)-1-chloro-3-phenyl-3-(2-methoxyphenoxy)propane

methylamine

Refernces

• 1、 Kamal, Ahmed,Khanna,Ramu. "Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles". . p. 2039 - 2051. Retrieved 2007/10/03.
• 2、 Schneider,Goergens. "An efficient route to enantiomerically pure antidepressants: Tomoxetine, nisoxetine and fluoxetine". . p. 525 - 528. Retrieved 2007/10/02.