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molecular formula C13H18ClNO B3031121 Bupropion D9 CAS No. 150988-80-0

Bupropion D9

Cat. No. B3031121
M. Wt: 248.79 g/mol
InChI Key: SNPPWIUOZRMYNY-WVZRYRIDSA-N
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Patent
US07737302B2

Procedure details

t-Butylamine was added to m-chloro-α-bromopropiophenone obtained above and the reaction mixture was refluxed for 3 hours. Excessive t-butylamine was removed by evaporation below 80° C. The concentrated solution was cooled down to room temperature and then extracted with 800 ml of ethyl acetate and 280 ml of water. The organic phase was dried with anhydrous magnesium sulfate (15 g) to obtain a solution of bupropion free base. A solution of HCl in ethyl acetate was added at room temperature to the organic phase. Crude product of bupropion hydrochloride was obtained after filtration. The crude product of bupropion hydrochloride was dissolved in 1200 ml of methanol and 120 ml of water at 80° C., decolorized with activated carbon (5 g) for 20 minutes and filtered. The filtrate was cooled and filtered to obtain wet product of bupropion hydrochloride. The wet product was dried in vacuum (−0.04˜−0.09 MPa, 80° C.) for 3 hours to obtain pure product. Total yield was 70% based on m-chloropropiophenone, and the HPLC's purify was higher than or equal to 99.9%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One

Identifiers

REACTION_CXSMILES
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:17])[CH:14](Br)[CH3:15])[CH:10]=[CH:11][CH:12]=1>>[CH3:15][CH:14]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)=[O:17]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)(C)N
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC=1C=C(C=CC1)C(C(C)Br)=O

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
obtained above and the reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
was refluxed for 3 hours
Duration
3 h
CUSTOM
Type
CUSTOM
Details
Excessive t-butylamine was removed by evaporation below 80° C
EXTRACTION
Type
EXTRACTION
Details
extracted with 800 ml of ethyl acetate and 280 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The organic phase was dried with anhydrous magnesium sulfate (15 g)

Outcomes

Product
Name
Type
product
Smiles
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C

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
US07737302B2

Procedure details

t-Butylamine was added to m-chloro-α-bromopropiophenone obtained above and the reaction mixture was refluxed for 3 hours. Excessive t-butylamine was removed by evaporation below 80° C. The concentrated solution was cooled down to room temperature and then extracted with 800 ml of ethyl acetate and 280 ml of water. The organic phase was dried with anhydrous magnesium sulfate (15 g) to obtain a solution of bupropion free base. A solution of HCl in ethyl acetate was added at room temperature to the organic phase. Crude product of bupropion hydrochloride was obtained after filtration. The crude product of bupropion hydrochloride was dissolved in 1200 ml of methanol and 120 ml of water at 80° C., decolorized with activated carbon (5 g) for 20 minutes and filtered. The filtrate was cooled and filtered to obtain wet product of bupropion hydrochloride. The wet product was dried in vacuum (−0.04˜−0.09 MPa, 80° C.) for 3 hours to obtain pure product. Total yield was 70% based on m-chloropropiophenone, and the HPLC's purify was higher than or equal to 99.9%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One

Identifiers

REACTION_CXSMILES
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:17])[CH:14](Br)[CH3:15])[CH:10]=[CH:11][CH:12]=1>>[CH3:15][CH:14]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)=[O:17]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)(C)N
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC=1C=C(C=CC1)C(C(C)Br)=O

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
obtained above and the reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
was refluxed for 3 hours
Duration
3 h
CUSTOM
Type
CUSTOM
Details
Excessive t-butylamine was removed by evaporation below 80° C
EXTRACTION
Type
EXTRACTION
Details
extracted with 800 ml of ethyl acetate and 280 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The organic phase was dried with anhydrous magnesium sulfate (15 g)

Outcomes

Product
Name
Type
product
Smiles
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C

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
US07737302B2

Procedure details

t-Butylamine was added to m-chloro-α-bromopropiophenone obtained above and the reaction mixture was refluxed for 3 hours. Excessive t-butylamine was removed by evaporation below 80° C. The concentrated solution was cooled down to room temperature and then extracted with 800 ml of ethyl acetate and 280 ml of water. The organic phase was dried with anhydrous magnesium sulfate (15 g) to obtain a solution of bupropion free base. A solution of HCl in ethyl acetate was added at room temperature to the organic phase. Crude product of bupropion hydrochloride was obtained after filtration. The crude product of bupropion hydrochloride was dissolved in 1200 ml of methanol and 120 ml of water at 80° C., decolorized with activated carbon (5 g) for 20 minutes and filtered. The filtrate was cooled and filtered to obtain wet product of bupropion hydrochloride. The wet product was dried in vacuum (−0.04˜−0.09 MPa, 80° C.) for 3 hours to obtain pure product. Total yield was 70% based on m-chloropropiophenone, and the HPLC's purify was higher than or equal to 99.9%.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One

Identifiers

REACTION_CXSMILES
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13](=[O:17])[CH:14](Br)[CH3:15])[CH:10]=[CH:11][CH:12]=1>>[CH3:15][CH:14]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)=[O:17]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C)(C)(C)N
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC=1C=C(C=CC1)C(C(C)Br)=O

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
obtained above and the reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
was refluxed for 3 hours
Duration
3 h
CUSTOM
Type
CUSTOM
Details
Excessive t-butylamine was removed by evaporation below 80° C
EXTRACTION
Type
EXTRACTION
Details
extracted with 800 ml of ethyl acetate and 280 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The organic phase was dried with anhydrous magnesium sulfate (15 g)

Outcomes

Product
Name
Type
product
Smiles
CC(C(=O)C=1C=CC=C(C1)Cl)NC(C)(C)C

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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