Reboxetine

Base Information

• Chemical Name: Reboxetine
• CAS No.: 71620-89-8
• Deprecated CAS: 98769-81-4,98769-83-6,71621-36-8
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• UNII: 947S0YZ36I
• DSSTox Substance ID: DTXSID1048257,DTXSID401315414
• Nikkaji Number: J569.655K
• Wikipedia: Reboxetine
• Wikidata: Q72506458
• NCI Thesaurus Code: C72838
• Pharos Ligand ID: C7VKFVTWLVPU
• ChEMBL ID: CHEMBL383921
• Mol file: 71620-89-8.mol

Synonyms:2-((2-ethoxyphenoxy)benzyl)morpholine methanesulfonate;reboxetine;reboxetine mesylate;Vestra

Chemical Property of Reboxetine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.54E-08mmHg at 25°C
• Melting Point: 141-143oC
• Boiling Point: 443.7 °C at 760 mmHg
• PKA: 8.37±0.40(Predicted)
• Flash Point: 188.2 °C
• PSA: 39.72000
• Density: 1.113 g/cm³
• LogP: 3.52260
• Storage Temp.: Desiccate at +4°C
• Solubility.: Chloroform (Slightly), Water (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 333

Purity/Quality:

98%,99%, ^*data from raw suppliers

Reboxetine, Mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1OC(C2CNCCO2)C3=CC=CC=C3
• Isomeric SMILES: CCOC1=CC=CC=C1O[C@@H]([C@H]2CNCCO2)C3=CC=CC=C3
• Recent ClinicalTrials: Efficacy of Reboxetine and Methylphenidate Treatment on Attentional, Sensory and Emotional Dysregulation in Adults With PTSD
• Recent EU Clinical Trials: The effect of various medications on emotioal processing, attention, experiences and sensory information processing
• Uses: Antidepressant (selective noradrenaline reuptake inhibitor). Reboxetine can be used in biological study of the involvement of monoaminergic neurotransmission in the antidepressant-like action of scopolamine in the tail suspension test.

Technology Process of Reboxetine

There total 108 articles about Reboxetine 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:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one (93886-32-9,98769-79-0,98769-80-3,98819-75-1) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

trans-2,3-epoxy-3-phenylpropan-1-ol (40641-81-4) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaOH / 1.) H₂O, 70 deg C; 2.) H₂O, 70 deg C, 2.5 h

2: 61 percent / pyridine / 2 h / -10 °C

3: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 5 °C

4: 2N NaOH / dioxane / 4 h / Ambient temperature

5: 32percent NH₄OH / methanol / 6 h / sealed flask

6: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

7: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

8: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; sodium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,4-dioxane; pyridine; methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

(2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8) → reboxetine (71620-89-8,71621-36-8,93851-86-6,98769-81-4,98769-83-6,98819-76-2,105017-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 32percent NH₄OH / methanol / 6 h / sealed flask

2: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / -10 - -5 °C

3: 86 percent / t-BuOK / 2-methyl-propan-2-ol / 3 h / Ambient temperature

4: RED-AL / toluene / 4 h / Ambient temperature

With ammonium hydroxide; potassium tert-butylate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In methanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)96541-X

upstream raw materials:

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one

2-Ethoxyphenol

benzaldehyde

trans-2,3-epoxy-3-phenylpropan-1-ol

Downstream raw materials:

(S,S)-reboxetine

(2R,3R)-reboxetine

(S,S)-reboxetine (S)-mandelate

(2S,3S)-2-[α-(2-ethoxyphenoxy)benzyl]morpholine succinate

Refernces

• 1、 -. "Sulfoxide ligand metal catalyzed oxidation of olefins". Page/Page column 171. . Retrieved 2019/05/09.
• 2、 Liu, Cheng,Lin, Zhi-Wei,Zhou, Zhao-Hui,Chen, Hong-Bin. "Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine". . p. 5395 - 5401. Retrieved 2017/07/10.