molecular formula C17H18F3NO B1224025 (R)-Fluoxetine CAS No. 100568-03-4

(R)-Fluoxetine

Cat. No.: B1224025
CAS No.: 100568-03-4
M. Wt: 309.33 g/mol
InChI Key: RTHCYVBBDHJXIQ-MRXNPFEDSA-N
Attention: For research use only. Not for human or veterinary use.
In Stock
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.

Description

(R)-fluoxetine is an N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has R configuration. [The antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine]. It has a role as an antidepressant and a serotonin uptake inhibitor. It is a conjugate base of a this compound(1+). It is an enantiomer of a (S)-fluoxetine.
An N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine that has R configuration (the antidepressant drug fluoxetine is a racemate comprising equimolar amounts of (R)- and (S)-fluoxetine).

Properties

IUPAC Name

(3R)-N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C17H18F3NO/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20/h2-10,16,21H,11-12H2,1H3/t16-/m1/s1
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

RTHCYVBBDHJXIQ-MRXNPFEDSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CNCCC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Isomeric SMILES

CNCC[C@H](C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C17H18F3NO
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

DSSTOX Substance ID

DTXSID10872290
Record name (R)-(+)-Fluoxetine
Source EPA DSSTox
URL https://comptox.epa.gov/dashboard/DTXSID10872290
Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight

309.33 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

CAS No.

100568-03-4
Record name (+)-Fluoxetine
Source CAS Common Chemistry
URL https://commonchemistry.cas.org/detail?cas_rn=100568-03-4
Description CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
Record name Fluoxetine, (R)-
Source ChemIDplus
URL https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0100568034
Description ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.
Record name (R)-Fluoxetine
Source DrugBank
URL https://www.drugbank.ca/drugs/DB08472
Description The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
Record name (R)-(+)-Fluoxetine
Source EPA DSSTox
URL https://comptox.epa.gov/dashboard/DTXSID10872290
Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.
Record name FLUOXETINE, (R)-
Source FDA Global Substance Registration System (GSRS)
URL https://gsrs.ncats.nih.gov/ginas/app/beta/substances/F279341RUQ
Description The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions.
Explanation Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.

Synthesis routes and methods I

Procedure details

An improved process for the preparation in a superior yield of N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine of formula (I), ##STR5## or a pharmaceutically acceptable acid addition salt thereof, the said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR6## to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III), ##STR7## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR8## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of a potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six

Synthesis routes and methods II

Procedure details

An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six
[Compound]
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight
[Compound]
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten

Synthesis routes and methods III

Procedure details

A mixture of 4.0 g (0.0357 mol) potassium t-butoxide, ml of N-methylpyrrolidone, 5.0 g (0.0303 mol) of 1-phenyl-3-N-methylaminopropan-1-ol, and 7.4 g (0.0410 mol) of 1-chloro-4-trifluoromethylbenzene was heated to 40° C. and stirred for 8 hours at 40° C. The mixture was then cooled to 20°-25° C. and 40 ml of toluene and water were added. The combined toluene-phases were washed four times with 20 ml of water. Toluene was evaporated under reduced pressure yielding 5.06 g of the product.
Quantity
4 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Reaction Step One
Quantity
7.4 g
Type
reactant
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Synthesis routes and methods IV

Procedure details

reducing said N-[3-[4-(trifluoromethyl)phenoxy]-3-phenylpropyl)urethane with borane or a metal hydride to provide N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine.
Name
N-[3-[4-(trifluoromethyl)phenoxy]-3-phenylpropyl)urethane
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

Reactant of Route 1
Reactant of Route 1
(R)-Fluoxetine
Reactant of Route 2
Reactant of Route 2
(R)-Fluoxetine
Reactant of Route 3
Reactant of Route 3
(R)-Fluoxetine
Reactant of Route 4
Reactant of Route 4
(R)-Fluoxetine
Reactant of Route 5
Reactant of Route 5
(R)-Fluoxetine
Reactant of Route 6
Reactant of Route 6
(R)-Fluoxetine

Disclaimer and Information on In-Vitro Research Products

Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.