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

(R)-(-)-citalopram

Katalognummer B155561
Molekulargewicht: 324.4 g/mol
InChI-Schlüssel: WSEQXVZVJXJVFP-HXUWFJFHSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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Patent
US06310222B1

Procedure details

60% Sodium hydride (0.92 g) was dispersed in THF (30 ml). To the obtained suspension was added dropwise a solution of 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (4.80 g) in THF (10 ml) at 40-50° C. The mixture was stirred at the same temperature for 30 min, and a solution of 3-dimethylaminopropyl chloride (3.2 g) in toluene (20 ml) was added dropwise, which was followed by stirring for 10 min. Then, dimethyl sulfoxide (30 ml) was further added dropwise and the mixture was stirred at 65-70° C. for 3 hr. The reaction mixture was poured into ice water (200 ml) and extracted 3 times with toluene (60 ml). The organic layer was extracted twice with 20% aqueous acetic acid (60 ml). The aqueous layer was neutralized, extracted twice with toluene (60 ml) and washed with water. Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added and the mixture was stirred and filtered. The solvent was evaporated to give 1-(3′-dimethylaminopropyl)-1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram base) as a viscous oil (3.37 g, 51.6%).
Quantity
0.92 g
Type
reactant
Reaction Step One
Name
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
4.8 g
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Two
Quantity
3.2 g
Type
reactant
Reaction Step Three
Quantity
20 mL
Type
solvent
Reaction Step Three
Quantity
30 mL
Type
reactant
Reaction Step Four
[Compound]
Name
ice water
Quantity
200 mL
Type
reactant
Reaction Step Five

Identifiers

REACTION_CXSMILES
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=3)[CH2:12][O:11]2)=[CH:6][CH:5]=1.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl.CS(C)=O>C1COCC1.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH2:12][O:11]1 |f:0.1|

Inputs

Step One
Name
Quantity
0.92 g
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
30 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
4.8 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1OCC2=CC(=CC=C12)C#N
Name
Quantity
10 mL
Type
solvent
Smiles
C1CCOC1
Step Three
Name
Quantity
3.2 g
Type
reactant
Smiles
CN(CCCCl)C
Name
Quantity
20 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Four
Name
Quantity
30 mL
Type
reactant
Smiles
CS(=O)C
Step Five
Name
ice water
Quantity
200 mL
Type
reactant
Smiles

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred at the same temperature for 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

STIRRING
Type
STIRRING
Details
by stirring for 10 min
Duration
10 min
STIRRING
Type
STIRRING
Details
the mixture was stirred at 65-70° C. for 3 hr
Duration
3 h
EXTRACTION
Type
EXTRACTION
Details
extracted 3 times with toluene (60 ml)
EXTRACTION
Type
EXTRACTION
Details
The organic layer was extracted twice with 20% aqueous acetic acid (60 ml)
EXTRACTION
Type
EXTRACTION
Details
extracted twice with toluene (60 ml)
WASH
Type
WASH
Details
washed with water
ADDITION
Type
ADDITION
Details
Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added
STIRRING
Type
STIRRING
Details
the mixture was stirred
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The solvent was evaporated

Outcomes

Product
Details
Reaction Time
30 min
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 3.37 g
YIELD: PERCENTYIELD 51.6%
YIELD: CALCULATEDPERCENTYIELD 51.8%

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
US06310222B1

Procedure details

60% Sodium hydride (0.92 g) was dispersed in THF (30 ml). To the obtained suspension was added dropwise a solution of 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (4.80 g) in THF (10 ml) at 40-50° C. The mixture was stirred at the same temperature for 30 min, and a solution of 3-dimethylaminopropyl chloride (3.2 g) in toluene (20 ml) was added dropwise, which was followed by stirring for 10 min. Then, dimethyl sulfoxide (30 ml) was further added dropwise and the mixture was stirred at 65-70° C. for 3 hr. The reaction mixture was poured into ice water (200 ml) and extracted 3 times with toluene (60 ml). The organic layer was extracted twice with 20% aqueous acetic acid (60 ml). The aqueous layer was neutralized, extracted twice with toluene (60 ml) and washed with water. Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added and the mixture was stirred and filtered. The solvent was evaporated to give 1-(3′-dimethylaminopropyl)-1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram base) as a viscous oil (3.37 g, 51.6%).
Quantity
0.92 g
Type
reactant
Reaction Step One
Name
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
4.8 g
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Two
Quantity
3.2 g
Type
reactant
Reaction Step Three
Quantity
20 mL
Type
solvent
Reaction Step Three
Quantity
30 mL
Type
reactant
Reaction Step Four
[Compound]
Name
ice water
Quantity
200 mL
Type
reactant
Reaction Step Five

Identifiers

REACTION_CXSMILES
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=3)[CH2:12][O:11]2)=[CH:6][CH:5]=1.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl.CS(C)=O>C1COCC1.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH2:12][O:11]1 |f:0.1|

Inputs

Step One
Name
Quantity
0.92 g
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
30 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
4.8 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1OCC2=CC(=CC=C12)C#N
Name
Quantity
10 mL
Type
solvent
Smiles
C1CCOC1
Step Three
Name
Quantity
3.2 g
Type
reactant
Smiles
CN(CCCCl)C
Name
Quantity
20 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Four
Name
Quantity
30 mL
Type
reactant
Smiles
CS(=O)C
Step Five
Name
ice water
Quantity
200 mL
Type
reactant
Smiles

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred at the same temperature for 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

STIRRING
Type
STIRRING
Details
by stirring for 10 min
Duration
10 min
STIRRING
Type
STIRRING
Details
the mixture was stirred at 65-70° C. for 3 hr
Duration
3 h
EXTRACTION
Type
EXTRACTION
Details
extracted 3 times with toluene (60 ml)
EXTRACTION
Type
EXTRACTION
Details
The organic layer was extracted twice with 20% aqueous acetic acid (60 ml)
EXTRACTION
Type
EXTRACTION
Details
extracted twice with toluene (60 ml)
WASH
Type
WASH
Details
washed with water
ADDITION
Type
ADDITION
Details
Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added
STIRRING
Type
STIRRING
Details
the mixture was stirred
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The solvent was evaporated

Outcomes

Product
Details
Reaction Time
30 min
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 3.37 g
YIELD: PERCENTYIELD 51.6%
YIELD: CALCULATEDPERCENTYIELD 51.8%

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
US06310222B1

Procedure details

60% Sodium hydride (0.92 g) was dispersed in THF (30 ml). To the obtained suspension was added dropwise a solution of 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (4.80 g) in THF (10 ml) at 40-50° C. The mixture was stirred at the same temperature for 30 min, and a solution of 3-dimethylaminopropyl chloride (3.2 g) in toluene (20 ml) was added dropwise, which was followed by stirring for 10 min. Then, dimethyl sulfoxide (30 ml) was further added dropwise and the mixture was stirred at 65-70° C. for 3 hr. The reaction mixture was poured into ice water (200 ml) and extracted 3 times with toluene (60 ml). The organic layer was extracted twice with 20% aqueous acetic acid (60 ml). The aqueous layer was neutralized, extracted twice with toluene (60 ml) and washed with water. Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added and the mixture was stirred and filtered. The solvent was evaporated to give 1-(3′-dimethylaminopropyl)-1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram base) as a viscous oil (3.37 g, 51.6%).
Quantity
0.92 g
Type
reactant
Reaction Step One
Name
Quantity
30 mL
Type
solvent
Reaction Step One
Quantity
4.8 g
Type
reactant
Reaction Step Two
Name
Quantity
10 mL
Type
solvent
Reaction Step Two
Quantity
3.2 g
Type
reactant
Reaction Step Three
Quantity
20 mL
Type
solvent
Reaction Step Three
Quantity
30 mL
Type
reactant
Reaction Step Four
[Compound]
Name
ice water
Quantity
200 mL
Type
reactant
Reaction Step Five

Identifiers

REACTION_CXSMILES
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=3)[CH2:12][O:11]2)=[CH:6][CH:5]=1.[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25]Cl.CS(C)=O>C1COCC1.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][C:10]1([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[C:18]2[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=2)[CH2:12][O:11]1 |f:0.1|

Inputs

Step One
Name
Quantity
0.92 g
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
30 mL
Type
solvent
Smiles
C1CCOC1
Step Two
Name
Quantity
4.8 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1OCC2=CC(=CC=C12)C#N
Name
Quantity
10 mL
Type
solvent
Smiles
C1CCOC1
Step Three
Name
Quantity
3.2 g
Type
reactant
Smiles
CN(CCCCl)C
Name
Quantity
20 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Four
Name
Quantity
30 mL
Type
reactant
Smiles
CS(=O)C
Step Five
Name
ice water
Quantity
200 mL
Type
reactant
Smiles

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred at the same temperature for 30 min
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

STIRRING
Type
STIRRING
Details
by stirring for 10 min
Duration
10 min
STIRRING
Type
STIRRING
Details
the mixture was stirred at 65-70° C. for 3 hr
Duration
3 h
EXTRACTION
Type
EXTRACTION
Details
extracted 3 times with toluene (60 ml)
EXTRACTION
Type
EXTRACTION
Details
The organic layer was extracted twice with 20% aqueous acetic acid (60 ml)
EXTRACTION
Type
EXTRACTION
Details
extracted twice with toluene (60 ml)
WASH
Type
WASH
Details
washed with water
ADDITION
Type
ADDITION
Details
Anhydrous potassium carbonate (2 g) and silica gel (2 g) were added
STIRRING
Type
STIRRING
Details
the mixture was stirred
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The solvent was evaporated

Outcomes

Product
Details
Reaction Time
30 min
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 3.37 g
YIELD: PERCENTYIELD 51.6%
YIELD: CALCULATEDPERCENTYIELD 51.8%

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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