(R)-Fluoxetine

Número de catálogo: B1224025

Número CAS: 100568-03-4

Peso molecular: 309.33 g/mol

Clave InChI: RTHCYVBBDHJXIQ-MRXNPFEDSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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Descripción general

1. Descripción

5. Synthesis routes and methods III

2. Propiedades

6. Synthesis routes and methods IV

3. Synthesis routes and methods I

7. Retrosynthesis analysis

4. Synthesis routes and methods II

8. Descargo de responsabilidad

Descripción

(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).

Propiedades

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

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

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

DSSTOX Substance ID	DTXSID10872290	Source
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
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	100568-03-4	Source
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.

Name

( III )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

1-chloro-4-trifluoromethylbenzene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

[Compound]

Name

( IV )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

N-methylpyrrolidone

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

potassium t-butoxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

dimethylsulfoxide

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Six

Name

N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine

Yield

85%

Details

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.

Name

1-chloro-4-trifluoromethylbenzene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

[Compound]

Name

( IV )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

potassium t-butoxide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

[H][H]

Name

hydrogen

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

1-phenyl-3-(N-methylamino)-propan-1-ol

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

( III )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

ethyl acetate

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Four

Name

Pt/C

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Four

Name

Pd/C

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Four

Name

Pd Pt/C

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Four

Name

dimethylsulfoxide

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Five

Name

N-methylpyrrolidone

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

Name

( III )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Ten

Name

N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine

Yield

85%

Details

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.

Name

potassium t-butoxide

Quantity

4 g

Type

reactant

Reaction Step One

Name

N-methylpyrrolidone

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

Name

1-chloro-4-trifluoromethylbenzene

Quantity

7.4 g

Type

reactant

Reaction Step One

Name

toluene

Quantity

40 mL

Type

reactant

Reaction Step Two

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Two

Name

product

Details

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

Name

borane

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

[Compound]

Name

metal hydride

Name

N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine

Details

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

(R)-Fluoxetine

Reactant of Route 2

(R)-Fluoxetine

Reactant of Route 3

(R)-Fluoxetine

Reactant of Route 4

(R)-Fluoxetine

Reactant of Route 5

(R)-Fluoxetine

Reactant of Route 6

(R)-Fluoxetine

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Tenga en cuenta que todos los artículos e información de productos presentados en BenchChem están destinados únicamente con fines informativos. Los productos disponibles para la compra en BenchChem están diseñados específicamente para estudios in vitro, que se realizan fuera de organismos vivos. Los estudios in vitro, derivados del término latino "in vidrio", involucran experimentos realizados en entornos de laboratorio controlados utilizando células o tejidos. Es importante tener en cuenta que estos productos no se clasifican como medicamentos y no han recibido la aprobación de la FDA para la prevención, tratamiento o cura de ninguna condición médica, dolencia o enfermedad. Debemos enfatizar que cualquier forma de introducción corporal de estos productos en humanos o animales está estrictamente prohibida por ley. Es esencial adherirse a estas pautas para garantizar el cumplimiento de los estándares legales y éticos en la investigación y experimentación.

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