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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 3-dimethylaminopropylmagnesium chloride (1.2M in THF, 84 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (25.0 g) in a mixture of toluene (175 ml) and THF (50 ml) so that the temperature did not raise above −5° C. The mixture was stirred for 2 hours at 0° C. before water (100 ml) and saturated NH4Cl solution were added to adjust the pH to 9. The phases were separated and the aqueous phase was extracted twice with toluene (200 ml). The combined organic phases were washed with water (200 ml) and concentrated in vacuo to give a viscous oil (28.0 g, 95%). Spectral and analytical data were in accordance with the literature.
Quantity
84 mL
Type
reactant
Reaction Step One
Quantity
25 g
Type
reactant
Reaction Step One
Quantity
175 mL
Type
solvent
Reaction Step One
Name
Quantity
50 mL
Type
solvent
Reaction Step One
Name
Quantity
100 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
95%

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].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[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 |f:3.4|

Inputs

Step One
Name
Quantity
84 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
25 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
175 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Name
Quantity
50 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
100 mL
Type
reactant
Smiles
O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[NH4+].[Cl-]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −5° C
ADDITION
Type
ADDITION
Details
were added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (200 ml)
WASH
Type
WASH
Details
The combined organic phases were washed with water (200 ml)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated 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 28 g
YIELD: PERCENTYIELD 95%

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 3-dimethylaminopropylmagnesium chloride (1.2M in THF, 84 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (25.0 g) in a mixture of toluene (175 ml) and THF (50 ml) so that the temperature did not raise above −5° C. The mixture was stirred for 2 hours at 0° C. before water (100 ml) and saturated NH4Cl solution were added to adjust the pH to 9. The phases were separated and the aqueous phase was extracted twice with toluene (200 ml). The combined organic phases were washed with water (200 ml) and concentrated in vacuo to give a viscous oil (28.0 g, 95%). Spectral and analytical data were in accordance with the literature.
Quantity
84 mL
Type
reactant
Reaction Step One
Quantity
25 g
Type
reactant
Reaction Step One
Quantity
175 mL
Type
solvent
Reaction Step One
Name
Quantity
50 mL
Type
solvent
Reaction Step One
Name
Quantity
100 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
95%

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].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[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 |f:3.4|

Inputs

Step One
Name
Quantity
84 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
25 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
175 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Name
Quantity
50 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
100 mL
Type
reactant
Smiles
O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[NH4+].[Cl-]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −5° C
ADDITION
Type
ADDITION
Details
were added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (200 ml)
WASH
Type
WASH
Details
The combined organic phases were washed with water (200 ml)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated 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 28 g
YIELD: PERCENTYIELD 95%

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 3-dimethylaminopropylmagnesium chloride (1.2M in THF, 84 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (25.0 g) in a mixture of toluene (175 ml) and THF (50 ml) so that the temperature did not raise above −5° C. The mixture was stirred for 2 hours at 0° C. before water (100 ml) and saturated NH4Cl solution were added to adjust the pH to 9. The phases were separated and the aqueous phase was extracted twice with toluene (200 ml). The combined organic phases were washed with water (200 ml) and concentrated in vacuo to give a viscous oil (28.0 g, 95%). Spectral and analytical data were in accordance with the literature.
Quantity
84 mL
Type
reactant
Reaction Step One
Quantity
25 g
Type
reactant
Reaction Step One
Quantity
175 mL
Type
solvent
Reaction Step One
Name
Quantity
50 mL
Type
solvent
Reaction Step One
Name
Quantity
100 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Yield
95%

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].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[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 |f:3.4|

Inputs

Step One
Name
Quantity
84 mL
Type
reactant
Smiles
CN(CCC[Mg]Cl)C
Name
Quantity
25 g
Type
reactant
Smiles
ClCC=1C=C(C#N)C=CC1C(C1=CC=C(C=C1)F)=O
Name
Quantity
175 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Name
Quantity
50 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
100 mL
Type
reactant
Smiles
O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[NH4+].[Cl-]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
did not raise above −5° C
ADDITION
Type
ADDITION
Details
were added
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted twice with toluene (200 ml)
WASH
Type
WASH
Details
The combined organic phases were washed with water (200 ml)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated 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 28 g
YIELD: PERCENTYIELD 95%

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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