![molecular formula C19H20FNO3 B3026791 (3R,4S)-3-[(2H-1,3-BENZODIOXOL-5-YLOXY)METHYL]-4-(4-FLUOROPHENYL)PIPERIDINE CAS No. 112058-85-2](/img/structure/B3026791.png)
(3R,4S)-3-[(2H-1,3-BENZODIOXOL-5-YLOXY)METHYL]-4-(4-FLUOROPHENYL)PIPERIDINE
カタログ番号 B3026791
分子量: 329.4 g/mol
InChIキー: AHOUBRCZNHFOSL-RHSMWYFYSA-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
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%.
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
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%.
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
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%.
Name
4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine-6-one
Quantity
0.41 g
Type
reactant
Reaction Step Two
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. |
