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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
Attention: For research use only. Not for human or veterinary use.
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Patent
US06660873B2

Procedure details

To a stirred solution of 5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (0.5 g, 1.5 mmol) in dichloromethane (10 mL) was added an aqueous solution of potassium bisulfate and sodium hydroxide (19 mL; 0.2 M in K2S2O8, 3.8 mmol; 0.4 M in NaOH, 7.6 mmol), followed by an aqueous solution of nickel sulfate (1.5 mL, 40 mM, 61 μmol). The mixture was stirred vigorously for 4 days, and was then filtered through celite. The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene. The aqueous layer was separated, and the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The solution was extracted with toluene, and this latter toluene extract was dried over magnesium sulfate and evaporated to give the free base of citalopram as a very pale yellow oil (0.35 g, 70%).
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
19 mL
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
1.5 mL
Type
catalyst
Reaction Step Two
Name
Yield
70%

Identifiers

REACTION_CXSMILES
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(=O)(=O)(O)[O-].[K+].[OH-].[Na+]>ClCCl.S([O-])([O-])(=O)=O.[Ni+2]>[CH3:23][N:22]([CH2:21][CH2:20][CH2:19][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[O:7][CH2:6][C:5]2[CH:4]=[C:3]([C:2]#[N:1])[CH:11]=[CH:10][C:9]1=2)[CH3:24] |f:1.2,3.4,6.7|

Inputs

Step One
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Smiles
NCC=1C=C2COC(C2=CC1)(C1=CC=C(C=C1)F)CCCN(C)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
S([O-])(O)(=O)=O.[K+]
Name
Quantity
19 mL
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Two
Name
Quantity
1.5 mL
Type
catalyst
Smiles
S(=O)(=O)([O-])[O-].[Ni+2]

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred vigorously for 4 days
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
was then filtered through celite
CUSTOM
Type
CUSTOM
Details
The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene
CUSTOM
Type
CUSTOM
Details
The aqueous layer was separated
ADDITION
Type
ADDITION
Details
the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v)
EXTRACTION
Type
EXTRACTION
Details
The solution was extracted with toluene
EXTRACTION
Type
EXTRACTION
Details
this latter toluene extract
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
was dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated

Outcomes

Product
Details
Reaction Time
4 d
Name
Type
product
Smiles
CN(C)CCCC1(C=2C=CC(=CC2CO1)C#N)C=3C=CC(=CC3)F
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 0.35 g
YIELD: PERCENTYIELD 70%

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
US06660873B2

Procedure details

To a stirred solution of 5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (0.5 g, 1.5 mmol) in dichloromethane (10 mL) was added an aqueous solution of potassium bisulfate and sodium hydroxide (19 mL; 0.2 M in K2S2O8, 3.8 mmol; 0.4 M in NaOH, 7.6 mmol), followed by an aqueous solution of nickel sulfate (1.5 mL, 40 mM, 61 μmol). The mixture was stirred vigorously for 4 days, and was then filtered through celite. The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene. The aqueous layer was separated, and the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The solution was extracted with toluene, and this latter toluene extract was dried over magnesium sulfate and evaporated to give the free base of citalopram as a very pale yellow oil (0.35 g, 70%).
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
19 mL
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
1.5 mL
Type
catalyst
Reaction Step Two
Name
Yield
70%

Identifiers

REACTION_CXSMILES
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(=O)(=O)(O)[O-].[K+].[OH-].[Na+]>ClCCl.S([O-])([O-])(=O)=O.[Ni+2]>[CH3:23][N:22]([CH2:21][CH2:20][CH2:19][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[O:7][CH2:6][C:5]2[CH:4]=[C:3]([C:2]#[N:1])[CH:11]=[CH:10][C:9]1=2)[CH3:24] |f:1.2,3.4,6.7|

Inputs

Step One
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Smiles
NCC=1C=C2COC(C2=CC1)(C1=CC=C(C=C1)F)CCCN(C)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
S([O-])(O)(=O)=O.[K+]
Name
Quantity
19 mL
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Two
Name
Quantity
1.5 mL
Type
catalyst
Smiles
S(=O)(=O)([O-])[O-].[Ni+2]

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred vigorously for 4 days
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
was then filtered through celite
CUSTOM
Type
CUSTOM
Details
The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene
CUSTOM
Type
CUSTOM
Details
The aqueous layer was separated
ADDITION
Type
ADDITION
Details
the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v)
EXTRACTION
Type
EXTRACTION
Details
The solution was extracted with toluene
EXTRACTION
Type
EXTRACTION
Details
this latter toluene extract
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
was dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated

Outcomes

Product
Details
Reaction Time
4 d
Name
Type
product
Smiles
CN(C)CCCC1(C=2C=CC(=CC2CO1)C#N)C=3C=CC(=CC3)F
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 0.35 g
YIELD: PERCENTYIELD 70%

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
US06660873B2

Procedure details

To a stirred solution of 5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (0.5 g, 1.5 mmol) in dichloromethane (10 mL) was added an aqueous solution of potassium bisulfate and sodium hydroxide (19 mL; 0.2 M in K2S2O8, 3.8 mmol; 0.4 M in NaOH, 7.6 mmol), followed by an aqueous solution of nickel sulfate (1.5 mL, 40 mM, 61 μmol). The mixture was stirred vigorously for 4 days, and was then filtered through celite. The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene. The aqueous layer was separated, and the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The solution was extracted with toluene, and this latter toluene extract was dried over magnesium sulfate and evaporated to give the free base of citalopram as a very pale yellow oil (0.35 g, 70%).
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
19 mL
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
1.5 mL
Type
catalyst
Reaction Step Two
Name
Yield
70%

Identifiers

REACTION_CXSMILES
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:7][CH2:6]2.S(=O)(=O)(O)[O-].[K+].[OH-].[Na+]>ClCCl.S([O-])([O-])(=O)=O.[Ni+2]>[CH3:23][N:22]([CH2:21][CH2:20][CH2:19][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[O:7][CH2:6][C:5]2[CH:4]=[C:3]([C:2]#[N:1])[CH:11]=[CH:10][C:9]1=2)[CH3:24] |f:1.2,3.4,6.7|

Inputs

Step One
Name
5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran
Quantity
0.5 g
Type
reactant
Smiles
NCC=1C=C2COC(C2=CC1)(C1=CC=C(C=C1)F)CCCN(C)C
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
S([O-])(O)(=O)=O.[K+]
Name
Quantity
19 mL
Type
reactant
Smiles
[OH-].[Na+]
Name
Quantity
10 mL
Type
solvent
Smiles
ClCCl
Step Two
Name
Quantity
1.5 mL
Type
catalyst
Smiles
S(=O)(=O)([O-])[O-].[Ni+2]

Conditions

Stirring
Type
CUSTOM
Details
The mixture was stirred vigorously for 4 days
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

FILTRATION
Type
FILTRATION
Details
was then filtered through celite
CUSTOM
Type
CUSTOM
Details
The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene
CUSTOM
Type
CUSTOM
Details
The aqueous layer was separated
ADDITION
Type
ADDITION
Details
the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v)
EXTRACTION
Type
EXTRACTION
Details
The solution was extracted with toluene
EXTRACTION
Type
EXTRACTION
Details
this latter toluene extract
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
was dried over magnesium sulfate
CUSTOM
Type
CUSTOM
Details
evaporated

Outcomes

Product
Details
Reaction Time
4 d
Name
Type
product
Smiles
CN(C)CCCC1(C=2C=CC(=CC2CO1)C#N)C=3C=CC(=CC3)F
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 0.35 g
YIELD: PERCENTYIELD 70%

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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