(+)-Tomoxetine

Base Information

• Chemical Name: (+)-Tomoxetine
• CAS No.: 105314-53-2
• Molecular Formula: C₁₇H₂₁NO
• Molecular Weight: 255.36
• UNII: 33ZZJ3T1SC
• DSSTox Substance ID: DTXSID50147075
• Wikidata: Q83012094
• ChEMBL ID: CHEMBL1442868
• Mol file: 105314-53-2.mol

Synonyms:(+)-Tomoxetine;105314-53-2;(S)-Tomoxetine;Atomoxetine Impurity B;(3S)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine;33ZZJ3T1SC;(S)-N-Methyl-3-phenyl-3-(o-tolyloxy)propan-1-amine;Atomoxetine S-isomer;Lopac-T-7947;UNII-33ZZJ3T1SC;ATOMOXETINE, (S)-;SCHEMBL2209541;CHEMBL1442868;DTXSID50147075;PDSP1_000505;PDSP2_000503;NCGC00016056-01;ATOMOXETINE S-ISOMER [USP IMPURITY];CS-0440287;S)-N-METHYL-3-(2-METHYLPHENOXY)-3-PHENYLPROPYLAMINE;BENZENEPROPANAMINE, N-METHYL-.GAMMA.-(2-METHYLPHENOXY)-, (.GAMMA.S)-

Chemical Property of (+)-Tomoxetine

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 255.162314293
• Heavy Atom Count: 19
• Complexity: 237

Purity/Quality:

> 95% ^*data from raw suppliers

(S)-Tomoxetine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=CC=C1OC(CCNC)C2=CC=CC=C2
• Isomeric SMILES: CC1=CC=CC=C1O[C@@H](CCNC)C2=CC=CC=C2

Technology Process of (+)-Tomoxetine

There total 76 articles about (+)-Tomoxetine 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: 96.0%

-(-)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane (114446-47-8) + methylamine (74-89-5) → (R)-tomoxetine (105314-52-1,105314-53-2,63940-51-2,83015-26-3)

Guidance literature:

In ethanol; water; at 130 ℃;

DOI:10.1016/j.tetlet.2004.11.052

Reference yield: 89.51%

2-Fluorotoluene (95-52-3) + (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8) → (R)-tomoxetine (105314-52-1,105314-53-2,63940-51-2,83015-26-3)

Guidance literature:

(R)-N-methyl-3-phenyl-3-hydroxypropylamine; With potassium hydroxide; In dimethyl sulfoxide; at 130 ℃; for 1h;

2-Fluorotoluene; In dimethyl sulfoxide; at 130 ℃;

Reference yield: 84.0%

(R)-N-(ethoxycarbonyl)-3-(2-methylphenoxy)-3-phenyl-1-propanamine → (R)-tomoxetine (105314-52-1,105314-53-2,63940-51-2,83015-26-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

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

upstream raw materials:

2-methylchlorobenzene

(R)-N-methyl-3-phenyl-3-hydroxypropylamine

(R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate

methylamine

Downstream raw materials:

S-rivastigmine-atomoxetine

(R)-atomoxetine oxalate

-(+)-tomoxetine hydrochloride

(+/-)-atomoxetine

Refernces

• 1、 -. "Preparation method of N-methyl-3-(2-methylphenoxy)amphetamine". Paragraph 0081-0092. . Retrieved 2021/09/04.
• 2、 -. "Preparation method of atomoxetine". Paragraph 0003; 0012; 0013. . Retrieved 2020/06/05.