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molecular formula C16H25NO3 B1240704 Tramadol N-Oxide

Tramadol N-Oxide

Cat. No. B1240704
M. Wt: 279.37 g/mol
InChI Key: HBXKSXMNNGHBEA-ZBFHGGJFSA-N
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Patent
US05223541

Procedure details

Tramadol N-oxide was prepared as set forth hereinafter. Tramadol hydrochloride (0.5 mol) was converted its free base in basified water (pH>9) and then extracted with ether. The solid was then heated under a high vacuum to remove as much water as possible to yield 131.5 g of material. The material was dissolved in methanol (500 mL) and 65 g of 30% H2O2 was added. The solution was stirred for 3 hours and then an additional 65 g of the 30% H2O2 was added. The reaction was stirred for 2.5 days at room temperature. Approximately 10 mg of PtO2 (use of Pt/C is suggested for its ease of removal) on carbon was then added to the reaction mixture, and very gentle foaming took place. An additional 10 mg of PtO2 was added and the reaction mixture was stirred overnight and then filtered thru filter aid. The filtrate was concentrated under vacuum while being heated to a temperature <40° C. The residue was taken up in methylene chloride. Since the methylene chloride solution contained some colloidial platinum, the solution was diluted with ethyl acetate to 1 L and filtered through a nylon filter membrane (0.45μ pore size) to yield a clear colorless filtrate. The filtrate was concentrated to 600 mL, and then ethyl acetate was added continuously to maintain a volume of 800 mL while the solution was heated until a vapor temperature of 74° C. was reached. The solution was then cooled to room temperature. The solid was collected by filtration, washed with ethyl acetate and dried in vacuo to yield 126.6 g of the tramadol N-oxide (mp. 159.5°-160° C.).
Quantity
0.5 mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[OH2:21]>>[CH3:3][N+:2]([O-:21])([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0.5 mol
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
extracted with ether
TEMPERATURE
Type
TEMPERATURE
Details
The solid was then heated under a high vacuum
CUSTOM
Type
CUSTOM
Details
to remove as much water as possible

Outcomes

Product
Name
Type
product
Smiles
C[N+](C)(CC1CCCCC1(C2=CC(=CC=C2)OC)O)[O-]
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 131.5 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
US05223541

Procedure details

Tramadol N-oxide was prepared as set forth hereinafter. Tramadol hydrochloride (0.5 mol) was converted its free base in basified water (pH>9) and then extracted with ether. The solid was then heated under a high vacuum to remove as much water as possible to yield 131.5 g of material. The material was dissolved in methanol (500 mL) and 65 g of 30% H2O2 was added. The solution was stirred for 3 hours and then an additional 65 g of the 30% H2O2 was added. The reaction was stirred for 2.5 days at room temperature. Approximately 10 mg of PtO2 (use of Pt/C is suggested for its ease of removal) on carbon was then added to the reaction mixture, and very gentle foaming took place. An additional 10 mg of PtO2 was added and the reaction mixture was stirred overnight and then filtered thru filter aid. The filtrate was concentrated under vacuum while being heated to a temperature <40° C. The residue was taken up in methylene chloride. Since the methylene chloride solution contained some colloidial platinum, the solution was diluted with ethyl acetate to 1 L and filtered through a nylon filter membrane (0.45μ pore size) to yield a clear colorless filtrate. The filtrate was concentrated to 600 mL, and then ethyl acetate was added continuously to maintain a volume of 800 mL while the solution was heated until a vapor temperature of 74° C. was reached. The solution was then cooled to room temperature. The solid was collected by filtration, washed with ethyl acetate and dried in vacuo to yield 126.6 g of the tramadol N-oxide (mp. 159.5°-160° C.).
Quantity
0.5 mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[OH2:21]>>[CH3:3][N+:2]([O-:21])([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0.5 mol
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
extracted with ether
TEMPERATURE
Type
TEMPERATURE
Details
The solid was then heated under a high vacuum
CUSTOM
Type
CUSTOM
Details
to remove as much water as possible

Outcomes

Product
Name
Type
product
Smiles
C[N+](C)(CC1CCCCC1(C2=CC(=CC=C2)OC)O)[O-]
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 131.5 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
US05223541

Procedure details

Tramadol N-oxide was prepared as set forth hereinafter. Tramadol hydrochloride (0.5 mol) was converted its free base in basified water (pH>9) and then extracted with ether. The solid was then heated under a high vacuum to remove as much water as possible to yield 131.5 g of material. The material was dissolved in methanol (500 mL) and 65 g of 30% H2O2 was added. The solution was stirred for 3 hours and then an additional 65 g of the 30% H2O2 was added. The reaction was stirred for 2.5 days at room temperature. Approximately 10 mg of PtO2 (use of Pt/C is suggested for its ease of removal) on carbon was then added to the reaction mixture, and very gentle foaming took place. An additional 10 mg of PtO2 was added and the reaction mixture was stirred overnight and then filtered thru filter aid. The filtrate was concentrated under vacuum while being heated to a temperature <40° C. The residue was taken up in methylene chloride. Since the methylene chloride solution contained some colloidial platinum, the solution was diluted with ethyl acetate to 1 L and filtered through a nylon filter membrane (0.45μ pore size) to yield a clear colorless filtrate. The filtrate was concentrated to 600 mL, and then ethyl acetate was added continuously to maintain a volume of 800 mL while the solution was heated until a vapor temperature of 74° C. was reached. The solution was then cooled to room temperature. The solid was collected by filtration, washed with ethyl acetate and dried in vacuo to yield 126.6 g of the tramadol N-oxide (mp. 159.5°-160° C.).
Quantity
0.5 mol
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[OH2:21]>>[CH3:3][N+:2]([O-:21])([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1] |f:0.1|

Inputs

Step One
Name
Quantity
0.5 mol
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
extracted with ether
TEMPERATURE
Type
TEMPERATURE
Details
The solid was then heated under a high vacuum
CUSTOM
Type
CUSTOM
Details
to remove as much water as possible

Outcomes

Product
Name
Type
product
Smiles
C[N+](C)(CC1CCCCC1(C2=CC(=CC=C2)OC)O)[O-]
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 131.5 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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