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molecular formula C17H18F3NO B1224025 (R)-Fluoxetine CAS No. 100568-03-4

(R)-Fluoxetine

Cat. No. B1224025
M. Wt: 309.33 g/mol
InChI Key: RTHCYVBBDHJXIQ-MRXNPFEDSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05166437

Procedure details

A mixture of 4.0 g (0.0357 mol) potassium t-butoxide, ml of N-methylpyrrolidone, 5.0 g (0.0303 mol) of 1-phenyl-3-N-methylaminopropan-1-ol, and 7.4 g (0.0410 mol) of 1-chloro-4-trifluoromethylbenzene was heated to 40° C. and stirred for 8 hours at 40° C. The mixture was then cooled to 20°-25° C. and 40 ml of toluene and water were added. The combined toluene-phases were washed four times with 20 ml of water. Toluene was evaporated under reduced pressure yielding 5.06 g of the product.
Quantity
4 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Reaction Step One
Quantity
7.4 g
Type
reactant
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O.ClC1C=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17]C=1.[C:25]1(C)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>O>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([C:12]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)[O:4][C:2]1[CH:5]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:3]=1 |f:0.1|

Inputs

Step One
Name
Quantity
4 g
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Smiles
Name
Quantity
7.4 g
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
Quantity
40 mL
Type
reactant
Smiles
C1(=CC=CC=C1)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
40 °C
Stirring
Type
CUSTOM
Details
stirred for 8 hours at 40° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was then cooled to 20°-25° C.
WASH
Type
WASH
Details
The combined toluene-phases were washed four times with 20 ml of water
CUSTOM
Type
CUSTOM
Details
Toluene was evaporated under reduced pressure

Outcomes

Product
Details
Reaction Time
8 h
Name
Type
product
Smiles
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Measurements
Type Value Analysis
AMOUNT: MASS 5.06 g

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
US05166437

Procedure details

A mixture of 4.0 g (0.0357 mol) potassium t-butoxide, ml of N-methylpyrrolidone, 5.0 g (0.0303 mol) of 1-phenyl-3-N-methylaminopropan-1-ol, and 7.4 g (0.0410 mol) of 1-chloro-4-trifluoromethylbenzene was heated to 40° C. and stirred for 8 hours at 40° C. The mixture was then cooled to 20°-25° C. and 40 ml of toluene and water were added. The combined toluene-phases were washed four times with 20 ml of water. Toluene was evaporated under reduced pressure yielding 5.06 g of the product.
Quantity
4 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Reaction Step One
Quantity
7.4 g
Type
reactant
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O.ClC1C=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17]C=1.[C:25]1(C)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>O>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([C:12]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)[O:4][C:2]1[CH:5]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:3]=1 |f:0.1|

Inputs

Step One
Name
Quantity
4 g
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Smiles
Name
Quantity
7.4 g
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
Quantity
40 mL
Type
reactant
Smiles
C1(=CC=CC=C1)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
40 °C
Stirring
Type
CUSTOM
Details
stirred for 8 hours at 40° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was then cooled to 20°-25° C.
WASH
Type
WASH
Details
The combined toluene-phases were washed four times with 20 ml of water
CUSTOM
Type
CUSTOM
Details
Toluene was evaporated under reduced pressure

Outcomes

Product
Details
Reaction Time
8 h
Name
Type
product
Smiles
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Measurements
Type Value Analysis
AMOUNT: MASS 5.06 g

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
US05166437

Procedure details

A mixture of 4.0 g (0.0357 mol) potassium t-butoxide, ml of N-methylpyrrolidone, 5.0 g (0.0303 mol) of 1-phenyl-3-N-methylaminopropan-1-ol, and 7.4 g (0.0410 mol) of 1-chloro-4-trifluoromethylbenzene was heated to 40° C. and stirred for 8 hours at 40° C. The mixture was then cooled to 20°-25° C. and 40 ml of toluene and water were added. The combined toluene-phases were washed four times with 20 ml of water. Toluene was evaporated under reduced pressure yielding 5.06 g of the product.
Quantity
4 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Reaction Step One
Quantity
7.4 g
Type
reactant
Reaction Step One
Quantity
40 mL
Type
reactant
Reaction Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O.ClC1C=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17]C=1.[C:25]1(C)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>O>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([C:12]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)[O:4][C:2]1[CH:5]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:3]=1 |f:0.1|

Inputs

Step One
Name
Quantity
4 g
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Name
1-phenyl-3-N-methylaminopropan-1-ol
Quantity
5 g
Type
reactant
Smiles
Name
Quantity
7.4 g
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
Quantity
40 mL
Type
reactant
Smiles
C1(=CC=CC=C1)C
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
40 °C
Stirring
Type
CUSTOM
Details
stirred for 8 hours at 40° C
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
The mixture was then cooled to 20°-25° C.
WASH
Type
WASH
Details
The combined toluene-phases were washed four times with 20 ml of water
CUSTOM
Type
CUSTOM
Details
Toluene was evaporated under reduced pressure

Outcomes

Product
Details
Reaction Time
8 h
Name
Type
product
Smiles
CNCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1
Measurements
Type Value Analysis
AMOUNT: MASS 5.06 g

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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