(R)-(-)-citalopram
货号 B155561
分子量: 324.4 g/mol
InChI 键: WSEQXVZVJXJVFP-HXUWFJFHSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US06753433B2
Procedure details
A solution of 4-fluoro phenylmagnesium bromide (0.7M in THF, 16 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (1.75 g) in toluene (20 ml) so that the temperature did not rise above 0° C. After 40 minutes a solution of 3-dimethylaminopropylmagnesium chloride (0.85M in THF, 10 ml) was added so that the temperature did not rise above 2° C. The mixture was stirred for 30 minutes, and water (30 ml) was added. The pH of the mixture was adjusted to 4.5, and the phases were separated. The pH of the aqueous phase was adjusted to 8 and extracted with toluene (30 ml) and 2-propanol (10 ml). The organic phase was concentrated in vacuo to give a viscous oil (1.5 g, 56%). Spectral and analytical data were in accordance with the literature.
Name
Yield
56%
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][Mg]Cl.O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][C:14]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[C:12](=[CH:20][C:19]([C:21]#[N:22])=[CH:18][CH:17]=2)[CH2:11][O:15]1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
16 mL
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC=C(C=C1)[Mg]Br
|
|
Name
|
|
|
Quantity
|
1.75 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCC1=C(C(=O)Cl)C=CC(=C1)C#N
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)C
|
Step Two
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(CCC[Mg]Cl)C
|
Step Three
|
Name
|
|
|
Quantity
|
30 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred for 30 minutes
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 0° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 2° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the phases were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted with toluene (30 ml) and 2-propanol (10 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The organic phase was concentrated in vacuo
|
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 | 1.5 g | |
| YIELD: PERCENTYIELD | 56% |
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 4-fluoro phenylmagnesium bromide (0.7M in THF, 16 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (1.75 g) in toluene (20 ml) so that the temperature did not rise above 0° C. After 40 minutes a solution of 3-dimethylaminopropylmagnesium chloride (0.85M in THF, 10 ml) was added so that the temperature did not rise above 2° C. The mixture was stirred for 30 minutes, and water (30 ml) was added. The pH of the mixture was adjusted to 4.5, and the phases were separated. The pH of the aqueous phase was adjusted to 8 and extracted with toluene (30 ml) and 2-propanol (10 ml). The organic phase was concentrated in vacuo to give a viscous oil (1.5 g, 56%). Spectral and analytical data were in accordance with the literature.
Name
Yield
56%
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][Mg]Cl.O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][C:14]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[C:12](=[CH:20][C:19]([C:21]#[N:22])=[CH:18][CH:17]=2)[CH2:11][O:15]1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
16 mL
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC=C(C=C1)[Mg]Br
|
|
Name
|
|
|
Quantity
|
1.75 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCC1=C(C(=O)Cl)C=CC(=C1)C#N
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)C
|
Step Two
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(CCC[Mg]Cl)C
|
Step Three
|
Name
|
|
|
Quantity
|
30 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred for 30 minutes
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 0° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 2° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the phases were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted with toluene (30 ml) and 2-propanol (10 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The organic phase was concentrated in vacuo
|
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 | 1.5 g | |
| YIELD: PERCENTYIELD | 56% |
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 4-fluoro phenylmagnesium bromide (0.7M in THF, 16 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (1.75 g) in toluene (20 ml) so that the temperature did not rise above 0° C. After 40 minutes a solution of 3-dimethylaminopropylmagnesium chloride (0.85M in THF, 10 ml) was added so that the temperature did not rise above 2° C. The mixture was stirred for 30 minutes, and water (30 ml) was added. The pH of the mixture was adjusted to 4.5, and the phases were separated. The pH of the aqueous phase was adjusted to 8 and extracted with toluene (30 ml) and 2-propanol (10 ml). The organic phase was concentrated in vacuo to give a viscous oil (1.5 g, 56%). Spectral and analytical data were in accordance with the literature.
Name
Yield
56%
Identifiers
|
REACTION_CXSMILES
|
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][Mg]Cl.O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][C:14]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[C:12](=[CH:20][C:19]([C:21]#[N:22])=[CH:18][CH:17]=2)[CH2:11][O:15]1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
16 mL
|
|
Type
|
reactant
|
|
Smiles
|
FC1=CC=C(C=C1)[Mg]Br
|
|
Name
|
|
|
Quantity
|
1.75 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCC1=C(C(=O)Cl)C=CC(=C1)C#N
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
C1(=CC=CC=C1)C
|
Step Two
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
CN(CCC[Mg]Cl)C
|
Step Three
|
Name
|
|
|
Quantity
|
30 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred for 30 minutes
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 0° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
did not rise above 2° C
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the phases were separated
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted with toluene (30 ml) and 2-propanol (10 ml)
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
The organic phase was concentrated in vacuo
|
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 | 1.5 g | |
| YIELD: PERCENTYIELD | 56% |
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. |
