(R)-(-)-citalopram
カタログ番号 B155561
分子量: 324.4 g/mol
InChIキー: WSEQXVZVJXJVFP-HXUWFJFHSA-N
注意: 研究専用です。人間または獣医用ではありません。
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
0.5 g
Type
reactant
Reaction Step One
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
0.5 g
Type
reactant
Reaction Step One
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
0.5 g
Type
reactant
Reaction Step One
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. |
