Bupropion D9
カタログ番号 B3031121
分子量: 248.79 g/mol
InChIキー: SNPPWIUOZRMYNY-WVZRYRIDSA-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
US08653271B2
Procedure details
1.0 g of bupropion hydrochloride salt was dissolved in the minimum amount of water in 250 ml flask. The contents of the flask were transferred to a separatory funnel, to which 20 ml of 10% aqueous sodium carbonate was added, and the mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (3×50 ml), then brine solution (50 ml), dried over anhydrous K2CO3, filtered and the filtrate stripped down under reduced pressure on a rotary evaporator to give the desired product as a yellow oil (7.9 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 7.90 (s, 1H), 7.81 (d, j=7.8 Hz, 1H), 7.48 (d, j=7.8 Hz, 1H), 7.37 (dd, j1=j2=7.8 Hz, 1H), 4.24 (qt, J=7.2 Hz, 1H), 1.19 (d, j=7.2 Hz, 3H), 0.97 (s, 9H) ppm. ppm; MS m/z 240 (M+). LC-MS m/z 240 (M+) single peak at Rt=8.40 min.
Name
Yield
90%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][CH:2]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][CH:2]([NH:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4] |f:0.1,2.3.4|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C.Cl
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the mixture was extracted with methylene chloride (3×50 ml)
|
WASH
|
Type
|
WASH
|
|
Details
|
The combined methylene chloride extracts were washed with water (3×50 ml)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
brine solution (50 ml), dried over anhydrous K2CO3
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the filtrate stripped down under reduced pressure on a rotary evaporator
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 7.9 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 910.1% |
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
US08653271B2
Procedure details
1.0 g of bupropion hydrochloride salt was dissolved in the minimum amount of water in 250 ml flask. The contents of the flask were transferred to a separatory funnel, to which 20 ml of 10% aqueous sodium carbonate was added, and the mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (3×50 ml), then brine solution (50 ml), dried over anhydrous K2CO3, filtered and the filtrate stripped down under reduced pressure on a rotary evaporator to give the desired product as a yellow oil (7.9 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 7.90 (s, 1H), 7.81 (d, j=7.8 Hz, 1H), 7.48 (d, j=7.8 Hz, 1H), 7.37 (dd, j1=j2=7.8 Hz, 1H), 4.24 (qt, J=7.2 Hz, 1H), 1.19 (d, j=7.2 Hz, 3H), 0.97 (s, 9H) ppm. ppm; MS m/z 240 (M+). LC-MS m/z 240 (M+) single peak at Rt=8.40 min.
Name
Yield
90%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][CH:2]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][CH:2]([NH:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4] |f:0.1,2.3.4|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C.Cl
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the mixture was extracted with methylene chloride (3×50 ml)
|
WASH
|
Type
|
WASH
|
|
Details
|
The combined methylene chloride extracts were washed with water (3×50 ml)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
brine solution (50 ml), dried over anhydrous K2CO3
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the filtrate stripped down under reduced pressure on a rotary evaporator
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 7.9 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 910.1% |
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
US08653271B2
Procedure details
1.0 g of bupropion hydrochloride salt was dissolved in the minimum amount of water in 250 ml flask. The contents of the flask were transferred to a separatory funnel, to which 20 ml of 10% aqueous sodium carbonate was added, and the mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (3×50 ml), then brine solution (50 ml), dried over anhydrous K2CO3, filtered and the filtrate stripped down under reduced pressure on a rotary evaporator to give the desired product as a yellow oil (7.9 g, 90% yield). 1H NMR (CDCl3, 400 MHz): δ 7.90 (s, 1H), 7.81 (d, j=7.8 Hz, 1H), 7.48 (d, j=7.8 Hz, 1H), 7.37 (dd, j1=j2=7.8 Hz, 1H), 4.24 (qt, J=7.2 Hz, 1H), 1.19 (d, j=7.2 Hz, 3H), 0.97 (s, 9H) ppm. ppm; MS m/z 240 (M+). LC-MS m/z 240 (M+) single peak at Rt=8.40 min.
Name
Yield
90%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][CH:2]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][CH:2]([NH:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4] |f:0.1,2.3.4|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
1 g
|
|
Type
|
reactant
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C.Cl
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
O
|
Step Two
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[Na+].[Na+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
ADDITION
|
Type
|
ADDITION
|
|
Details
|
was added
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the mixture was extracted with methylene chloride (3×50 ml)
|
WASH
|
Type
|
WASH
|
|
Details
|
The combined methylene chloride extracts were washed with water (3×50 ml)
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
brine solution (50 ml), dried over anhydrous K2CO3
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
filtered
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
the filtrate stripped down under reduced pressure on a rotary evaporator
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 7.9 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 910.1% |
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. |
