(R)-(-)-citalopram
Número de catálogo B155561
Peso molecular: 324.4 g/mol
Clave InChI: WSEQXVZVJXJVFP-HXUWFJFHSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
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.
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
|
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.
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
|
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.
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
|
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. |
