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molecular formula C16H26ClNO2 B3433423 2-(Dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol hydrochloride CAS No. 2914-78-5

2-(Dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol hydrochloride

Cat. No. B3433423
M. Wt: 299.83 g/mol
InChI Key: PPKXEPBICJTCRU-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07470816B2

Procedure details

In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Reaction Step One
Name
Quantity
87 mL
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
88 mL
Type
reactant
Reaction Step Three

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].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][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)[CH3:1].[ClH:34] |f:0.1,3.4,6.7|

Inputs

Step One
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.C(C=1C(O)=CC=CC1)(=O)[O-]
Name
Quantity
87 mL
Type
reactant
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Step Three
Name
Quantity
88 mL
Type
reactant
Smiles
C(Cl)Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Stirring
Type
CUSTOM
Details
Stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The tramadol free base was extracted with methylene chloride
EXTRACTION
Type
EXTRACTION
Details
organic extract
WASH
Type
WASH
Details
washed with water, and methylene chloride
CUSTOM
Type
CUSTOM
Details
was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
The oil obtained
STIRRING
Type
STIRRING
Details
Stirred for 1.0 hour at same temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
Raised the temperature to 25-30° C.
STIRRING
Type
STIRRING
Details
stirred it for 30 minutes
Duration
30 min
DISTILLATION
Type
DISTILLATION
Details
Distilled out solvent completely under vacuum
ADDITION
Type
ADDITION
Details
Charged 42 ml acetone
STIRRING
Type
STIRRING
Details
stirred at 25-30° C. for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the product
WASH
Type
WASH
Details
washed solid with acetone

Outcomes

Product
Name
Type
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl

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
US07470816B2

Procedure details

In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Reaction Step One
Name
Quantity
87 mL
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
88 mL
Type
reactant
Reaction Step Three

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].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][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)[CH3:1].[ClH:34] |f:0.1,3.4,6.7|

Inputs

Step One
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.C(C=1C(O)=CC=CC1)(=O)[O-]
Name
Quantity
87 mL
Type
reactant
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Step Three
Name
Quantity
88 mL
Type
reactant
Smiles
C(Cl)Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Stirring
Type
CUSTOM
Details
Stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The tramadol free base was extracted with methylene chloride
EXTRACTION
Type
EXTRACTION
Details
organic extract
WASH
Type
WASH
Details
washed with water, and methylene chloride
CUSTOM
Type
CUSTOM
Details
was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
The oil obtained
STIRRING
Type
STIRRING
Details
Stirred for 1.0 hour at same temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
Raised the temperature to 25-30° C.
STIRRING
Type
STIRRING
Details
stirred it for 30 minutes
Duration
30 min
DISTILLATION
Type
DISTILLATION
Details
Distilled out solvent completely under vacuum
ADDITION
Type
ADDITION
Details
Charged 42 ml acetone
STIRRING
Type
STIRRING
Details
stirred at 25-30° C. for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the product
WASH
Type
WASH
Details
washed solid with acetone

Outcomes

Product
Name
Type
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl

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
US07470816B2

Procedure details

In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Reaction Step One
Name
Quantity
87 mL
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
88 mL
Type
reactant
Reaction Step Three

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].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][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)[CH3:1].[ClH:34] |f:0.1,3.4,6.7|

Inputs

Step One
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.C(C=1C(O)=CC=CC1)(=O)[O-]
Name
Quantity
87 mL
Type
reactant
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Step Three
Name
Quantity
88 mL
Type
reactant
Smiles
C(Cl)Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Stirring
Type
CUSTOM
Details
Stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The tramadol free base was extracted with methylene chloride
EXTRACTION
Type
EXTRACTION
Details
organic extract
WASH
Type
WASH
Details
washed with water, and methylene chloride
CUSTOM
Type
CUSTOM
Details
was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
The oil obtained
STIRRING
Type
STIRRING
Details
Stirred for 1.0 hour at same temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
Raised the temperature to 25-30° C.
STIRRING
Type
STIRRING
Details
stirred it for 30 minutes
Duration
30 min
DISTILLATION
Type
DISTILLATION
Details
Distilled out solvent completely under vacuum
ADDITION
Type
ADDITION
Details
Charged 42 ml acetone
STIRRING
Type
STIRRING
Details
stirred at 25-30° C. for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the product
WASH
Type
WASH
Details
washed solid with acetone

Outcomes

Product
Name
Type
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl

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
US07470816B2

Procedure details

In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Reaction Step One
Name
Quantity
87 mL
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
88 mL
Type
reactant
Reaction Step Three

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].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][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)[CH3:1].[ClH:34] |f:0.1,3.4,6.7|

Inputs

Step One
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.C(C=1C(O)=CC=CC1)(=O)[O-]
Name
Quantity
87 mL
Type
reactant
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Step Three
Name
Quantity
88 mL
Type
reactant
Smiles
C(Cl)Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Stirring
Type
CUSTOM
Details
Stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The tramadol free base was extracted with methylene chloride
EXTRACTION
Type
EXTRACTION
Details
organic extract
WASH
Type
WASH
Details
washed with water, and methylene chloride
CUSTOM
Type
CUSTOM
Details
was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
The oil obtained
STIRRING
Type
STIRRING
Details
Stirred for 1.0 hour at same temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
Raised the temperature to 25-30° C.
STIRRING
Type
STIRRING
Details
stirred it for 30 minutes
Duration
30 min
DISTILLATION
Type
DISTILLATION
Details
Distilled out solvent completely under vacuum
ADDITION
Type
ADDITION
Details
Charged 42 ml acetone
STIRRING
Type
STIRRING
Details
stirred at 25-30° C. for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the product
WASH
Type
WASH
Details
washed solid with acetone

Outcomes

Product
Name
Type
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl

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
US07470816B2

Procedure details

In a reaction flask 29 g tramadol salicylate salt was stirred with 87 ml water and pH was adjusted to 11-12 by 10% aqueous KOH solution. The tramadol free base was extracted with methylene chloride, organic extract washed with water, and methylene chloride was evaporated under reduced pressure. The oil obtained was dissolved in 88.0 ml methylene chloride. Stirred and cooled to 15° C. Adjusted pH to 2-2.5 by conc. HCI. Stirred for 1.0 hour at same temperature. Raised the temperature to 25-30° C. and stirred it for 30 minutes. Distilled out solvent completely under vacuum. Charged 42 ml acetone and stirred at 25-30° C. for 30 minutes. Filtered the product and washed solid with acetone. Yield=18.4 gm (85%) (cis=99.98% & trans=0.02% by HPLC area%).
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Reaction Step One
Name
Quantity
87 mL
Type
reactant
Reaction Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
88 mL
Type
reactant
Reaction Step Three

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].C([O-])(=O)C1C(=CC=CC=1)O.O.[OH-].[K+].C(Cl)[Cl:34]>>[CH3:3][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)[CH3:1].[ClH:34] |f:0.1,3.4,6.7|

Inputs

Step One
Name
tramadol salicylate
Quantity
29 g
Type
reactant
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.C(C=1C(O)=CC=CC1)(=O)[O-]
Name
Quantity
87 mL
Type
reactant
Smiles
O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[K+]
Step Three
Name
Quantity
88 mL
Type
reactant
Smiles
C(Cl)Cl

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
15 °C
Stirring
Type
CUSTOM
Details
Stirred
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The tramadol free base was extracted with methylene chloride
EXTRACTION
Type
EXTRACTION
Details
organic extract
WASH
Type
WASH
Details
washed with water, and methylene chloride
CUSTOM
Type
CUSTOM
Details
was evaporated under reduced pressure
CUSTOM
Type
CUSTOM
Details
The oil obtained
STIRRING
Type
STIRRING
Details
Stirred for 1.0 hour at same temperature
Duration
1 h
TEMPERATURE
Type
TEMPERATURE
Details
Raised the temperature to 25-30° C.
STIRRING
Type
STIRRING
Details
stirred it for 30 minutes
Duration
30 min
DISTILLATION
Type
DISTILLATION
Details
Distilled out solvent completely under vacuum
ADDITION
Type
ADDITION
Details
Charged 42 ml acetone
STIRRING
Type
STIRRING
Details
stirred at 25-30° C. for 30 minutes
Duration
30 min
FILTRATION
Type
FILTRATION
Details
Filtered the product
WASH
Type
WASH
Details
washed solid with acetone

Outcomes

Product
Name
Type
Smiles
CN(C)CC1CCCCC1(C2=CC=CC(=C2)OC)O.Cl

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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