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molecular formula C20H21FN2O B155561 (R)-(-)-citalopram CAS No. 128196-02-1

(R)-(-)-citalopram

Cat. No. B155561
M. Wt: 324.4 g/mol
InChI Key: WSEQXVZVJXJVFP-HXUWFJFHSA-N
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Patent
US06753433B2

Procedure details

A solution of freshly prepared 3-dimethylaminopropylmagnesium chloride (0.6M in THF, 7.6 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (0.5 g) in ethylene glycol dimethyl ether (4 ml) so that the temperature did not raise above −4° C. The mixture was stirred for 30 minutes at −15° C. and 100 minutes at room temperature before 0.5N hydrobromic acid was added to adjust the pH to 10. The phases were separated and the aqueous phase was extracted twice with toluene (25 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a viscous oil (0.44 g, 75%). Spectral and analytical data were in accordance with the literature.
Quantity
7.6 mL
Type
reactant
Reaction Step One
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
4 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
75%

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14]#[N:15].Br>COCCOC>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:19]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]2[C:11](=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH2:10][O:27]1

Inputs

Step One
Name
Quantity
7.6 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
0.5 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
4 mL
Type
solvent
Smiles
COCCOC
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Br

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −4° C
ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (25 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases were dried over sodium sulfate
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
dried in vacuo

Outcomes

Product
Name
Type
product
Smiles
CN(CCCC1(OCC2=CC(=CC=C12)C#N)C1=CC=C(C=C1)F)C
Measurements
Type Value Analysis
AMOUNT: MASS 0.44 g
YIELD: PERCENTYIELD 75%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US06753433B2

Procedure details

A solution of freshly prepared 3-dimethylaminopropylmagnesium chloride (0.6M in THF, 7.6 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (0.5 g) in ethylene glycol dimethyl ether (4 ml) so that the temperature did not raise above −4° C. The mixture was stirred for 30 minutes at −15° C. and 100 minutes at room temperature before 0.5N hydrobromic acid was added to adjust the pH to 10. The phases were separated and the aqueous phase was extracted twice with toluene (25 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a viscous oil (0.44 g, 75%). Spectral and analytical data were in accordance with the literature.
Quantity
7.6 mL
Type
reactant
Reaction Step One
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
4 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
75%

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14]#[N:15].Br>COCCOC>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:19]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]2[C:11](=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH2:10][O:27]1

Inputs

Step One
Name
Quantity
7.6 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
0.5 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
4 mL
Type
solvent
Smiles
COCCOC
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Br

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −4° C
ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (25 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases were dried over sodium sulfate
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
dried in vacuo

Outcomes

Product
Name
Type
product
Smiles
CN(CCCC1(OCC2=CC(=CC=C12)C#N)C1=CC=C(C=C1)F)C
Measurements
Type Value Analysis
AMOUNT: MASS 0.44 g
YIELD: PERCENTYIELD 75%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US06753433B2

Procedure details

A solution of freshly prepared 3-dimethylaminopropylmagnesium chloride (0.6M in THF, 7.6 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (0.5 g) in ethylene glycol dimethyl ether (4 ml) so that the temperature did not raise above −4° C. The mixture was stirred for 30 minutes at −15° C. and 100 minutes at room temperature before 0.5N hydrobromic acid was added to adjust the pH to 10. The phases were separated and the aqueous phase was extracted twice with toluene (25 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a viscous oil (0.44 g, 75%). Spectral and analytical data were in accordance with the literature.
Quantity
7.6 mL
Type
reactant
Reaction Step One
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
4 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
75%

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14]#[N:15].Br>COCCOC>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:19]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]2[C:11](=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH2:10][O:27]1

Inputs

Step One
Name
Quantity
7.6 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
0.5 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
4 mL
Type
solvent
Smiles
COCCOC
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
Br

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −4° C
ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (25 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic phases were dried over sodium sulfate
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
dried in vacuo

Outcomes

Product
Name
Type
product
Smiles
CN(CCCC1(OCC2=CC(=CC=C12)C#N)C1=CC=C(C=C1)F)C
Measurements
Type Value Analysis
AMOUNT: MASS 0.44 g
YIELD: PERCENTYIELD 75%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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