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molecular formula C19H20FNO3 B3026791 (3R,4S)-3-[(2H-1,3-BENZODIOXOL-5-YLOXY)METHYL]-4-(4-FLUOROPHENYL)PIPERIDINE CAS No. 112058-85-2

(3R,4S)-3-[(2H-1,3-BENZODIOXOL-5-YLOXY)METHYL]-4-(4-FLUOROPHENYL)PIPERIDINE

Cat. No. B3026791
M. Wt: 329.4 g/mol
InChI Key: AHOUBRCZNHFOSL-RHSMWYFYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US06716985B2

Procedure details

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, 0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
Quantity
7 mL
Type
solvent
Reaction Step Two
Yield
90%

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1 |f:0.1.2.3.4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Name
Quantity
2 mL
Type
solvent
Smiles
O1CCCC1
Step Two
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1C(CNC(C1)=O)COC1=CC2=C(C=C1)OCO2
Name
Quantity
7 mL
Type
solvent
Smiles
O1CCCC1

Conditions

Stirring
Type
CUSTOM
Details
The reaction solution was stirred for 2 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature below 25° C
CUSTOM
Type
CUSTOM
Details
quenched first of all with water (0.16 ml)
STIRRING
Type
STIRRING
Details
The reaction mixture was stirred for 0.5 hours
Duration
0.5 h
CUSTOM
Type
CUSTOM
Details
the precipitation
ADDITION
Type
ADDITION
Details
diluted with dichloromethane (30 ml)
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The filtrate was evaporated in vacuo

Outcomes

Product
Details
Reaction Time
2 h
Name
Type
product
Smiles
FC1=CC=C(C=C1)C1C(CNCC1)COC1=CC2=C(C=C1)OCO2
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 90%

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
US06716985B2

Procedure details

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, 0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
Quantity
7 mL
Type
solvent
Reaction Step Two
Yield
90%

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1 |f:0.1.2.3.4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Name
Quantity
2 mL
Type
solvent
Smiles
O1CCCC1
Step Two
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1C(CNC(C1)=O)COC1=CC2=C(C=C1)OCO2
Name
Quantity
7 mL
Type
solvent
Smiles
O1CCCC1

Conditions

Stirring
Type
CUSTOM
Details
The reaction solution was stirred for 2 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature below 25° C
CUSTOM
Type
CUSTOM
Details
quenched first of all with water (0.16 ml)
STIRRING
Type
STIRRING
Details
The reaction mixture was stirred for 0.5 hours
Duration
0.5 h
CUSTOM
Type
CUSTOM
Details
the precipitation
ADDITION
Type
ADDITION
Details
diluted with dichloromethane (30 ml)
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The filtrate was evaporated in vacuo

Outcomes

Product
Details
Reaction Time
2 h
Name
Type
product
Smiles
FC1=CC=C(C=C1)C1C(CNCC1)COC1=CC2=C(C=C1)OCO2
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 90%

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
US06716985B2

Procedure details

A solution of lithium aluminium hydride in tetrahydrofuran (1.0M solution, 2 ml, 2.0 mmol) was added over ten minutes to a well stirred solution of 4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one (0.41 g, 0.96 mmol) in tetrahydrofuran (7 ml), maintaining the temperature below 25° C. The reaction solution was stirred for 2 hours and then quenched first of all with water (0.16 ml), then with 15% aqueous sodium hydroxide solution (0.1 ml), and finally with water again (0.4 ml). The reaction mixture was stirred for 0.5 hours to complete the precipitation, diluted with dichloromethane (30 ml) and filtered. The filtrate was evaporated in vacuo to give the title product with a trans/cis ratio=72:28. Yield 90%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
Quantity
7 mL
Type
solvent
Reaction Step Two
Yield
90%

Identifiers

REACTION_CXSMILES
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][C:18](=O)[NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)=[CH:10][CH:9]=1 |f:0.1.2.3.4.5|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H-].[Al+3].[Li+].[H-].[H-].[H-]
Name
Quantity
2 mL
Type
solvent
Smiles
O1CCCC1
Step Two
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Smiles
FC1=CC=C(C=C1)C1C(CNC(C1)=O)COC1=CC2=C(C=C1)OCO2
Name
Quantity
7 mL
Type
solvent
Smiles
O1CCCC1

Conditions

Stirring
Type
CUSTOM
Details
The reaction solution was stirred for 2 hours
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
maintaining the temperature below 25° C
CUSTOM
Type
CUSTOM
Details
quenched first of all with water (0.16 ml)
STIRRING
Type
STIRRING
Details
The reaction mixture was stirred for 0.5 hours
Duration
0.5 h
CUSTOM
Type
CUSTOM
Details
the precipitation
ADDITION
Type
ADDITION
Details
diluted with dichloromethane (30 ml)
FILTRATION
Type
FILTRATION
Details
filtered
CUSTOM
Type
CUSTOM
Details
The filtrate was evaporated in vacuo

Outcomes

Product
Details
Reaction Time
2 h
Name
Type
product
Smiles
FC1=CC=C(C=C1)C1C(CNCC1)COC1=CC2=C(C=C1)OCO2
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 90%

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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