Reboxetine mesylate

Base Information

• Chemical Name: Reboxetine mesylate
• CAS No.: 98769-84-7
• Deprecated CAS: 98769-82-5,141425-90-3
• Molecular Formula: CH₄O₃S*C₁₉H₂₃NO₃
• Molecular Weight: 409.503
• European Community (EC) Number: 638-822-2
• UNII: L94J81YNNY
• DSSTox Substance ID: DTXSID8045690
• Wikidata: Q27282861
• NCI Thesaurus Code: C152163
• ChEMBL ID: CHEMBL2105282
• Mol file: 98769-84-7.mol

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

Chemical Property of Reboxetine mesylate

Chemical Property:

• Appearance/Colour: tan or off-white cyrstalline solid
• Vapor Pressure: 4.54E-08mmHg at 25°C
• Melting Point: 170-171°C
• Boiling Point: 443.7 °C at 760 mmHg
• Flash Point: 188.2 °C
• PSA: 102.47000
• LogP: 4.10740
• Storage Temp.: 2-8°C
• Solubility.: H2O: ~8 mg/mL at ≤60 °C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 409.15590875
• Heavy Atom Count: 28
• Complexity: 425

Purity/Quality:

99%, ^*data from raw suppliers

ReboxetineMesylate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CCOC1=CC=CC=C1OC(C2CNCCO2)C3=CC=CC=C3.CS(=O)(=O)O
• Isomeric SMILES: CCOC1=CC=CC=C1O[C@@H]([C@H]2CNCCO2)C3=CC=CC=C3.CS(=O)(=O)O
• Recent EU Clinical Trials: Crossover, Double-blind, Phase 2 Study of a Fixed Dose Combination of Reboxetine\\Oxybutynin (AD128) Versus Placebo in Obstructive Sleep Apnea (RebOx)
• Uses: A selective noradrenaline reuptake inhibitor. Antidepressant. Reboxetine mesylate hydrate has been used as a selective norepinephrine transport blocker:to study its effects on the surge of dopamine in the cortex of mice brainto study its anti-immobility effects on the behavior of miceto analyze its effects on the probabilistic reversal learning task in rodents

Technology Process of Reboxetine mesylate

There total 19 articles about Reboxetine mesylate 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:

2-chloro-N-[3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]acetamide → Reboxetine mesylate (93851-87-7,98769-82-5,98769-84-7,98819-77-3,105017-39-8,141425-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / isopropyl alcohol; tert-butyl alcohol

2: methanesulfonic acid / acetone

With methanesulfonic acid; potassium tert-butylate; In isopropyl alcohol; acetone; tert-butyl alcohol;

DOI:10.1039/c1gc15921f

Reference yield:

(2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane methanesulfonate (93853-04-4,98769-75-6) → Reboxetine mesylate (93851-87-7,98769-82-5,98769-84-7,98819-77-3,105017-39-8,141425-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: carbonic acid dimethyl ester / ethanol

2: potassium tert-butylate / isopropyl alcohol; tert-butyl alcohol

3: methanesulfonic acid / acetone

With methanesulfonic acid; potassium tert-butylate; carbonic acid dimethyl ester; In ethanol; isopropyl alcohol; acetone; tert-butyl alcohol;

DOI:10.1039/c1gc15921f

Reference yield:

(2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8) → Reboxetine mesylate (93851-87-7,98769-82-5,98769-84-7,98819-77-3,105017-39-8,141425-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; ammonia / isopropyl alcohol

2: carbonic acid dimethyl ester / ethanol

3: potassium tert-butylate / isopropyl alcohol; tert-butyl alcohol

4: methanesulfonic acid / acetone

With methanol; methanesulfonic acid; potassium tert-butylate; ammonia; carbonic acid dimethyl ester; In ethanol; isopropyl alcohol; acetone; tert-butyl alcohol;

DOI:10.1039/c1gc15921f

upstream raw materials:

methanesulfonic acid

reboxetine

2-Ethoxyphenol

(2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane methanesulfonate

Refernces

• 1、 Henegar, Kevin E.,Ball, Cynthia T.,Horvath, Carolyn M.,Maisto, Keith D.,Mancini, Sarah E.. "Process development and scale-up for (±)-reboxetine mesylate". . p. 346 - 353. Retrieved 2012/12/31.