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molecular formula C10H15NO B041025 (R)-3-(methylamino)-1-phenylpropan-1-ol CAS No. 115290-81-8

(R)-3-(methylamino)-1-phenylpropan-1-ol

Cat. No. B041025
M. Wt: 165.23 g/mol
InChI Key: XXSDCGNHLFVSET-SNVBAGLBSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US05892117

Procedure details

2-Methyl-5-phenylisoxazolidine (2.0 g, 12.3 mmol) and Zn powder (1.2 g, 18.3 mmol) in 10 molar aqueous acetic acid are heated to 65°-70° C. for 4 hours. Additional Zn powder (0.4 g, 6.1 mmol) is added and heating is continued for one more hour. The reaction mixture is neutralized with sodium hydroxide and extracted with chloroform. The extract is dried (K2CO3) and concentrated to give N-methyl-3-phenyl-3-hydroxy-propyl-amine.
Quantity
2 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
Quantity
1.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0.4 g
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:3]1.[OH-].[Na+]>C(O)(=O)C.[Zn]>[CH3:1][NH:2][CH2:6][CH2:5][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3] |f:1.2|

Inputs

Step One
Name
Quantity
2 g
Type
reactant
Smiles
CN1OC(CC1)C1=CC=CC=C1
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)O
Name
Quantity
1.2 g
Type
catalyst
Smiles
[Zn]
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Three
Name
Quantity
0.4 g
Type
catalyst
Smiles
[Zn]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
heating
EXTRACTION
Type
EXTRACTION
Details
extracted with chloroform
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The extract is dried (K2CO3)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated

Outcomes

Product
Name
Type
product
Smiles
CNCCC(O)C1=CC=CC=C1

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
US05892117

Procedure details

2-Methyl-5-phenylisoxazolidine (2.0 g, 12.3 mmol) and Zn powder (1.2 g, 18.3 mmol) in 10 molar aqueous acetic acid are heated to 65°-70° C. for 4 hours. Additional Zn powder (0.4 g, 6.1 mmol) is added and heating is continued for one more hour. The reaction mixture is neutralized with sodium hydroxide and extracted with chloroform. The extract is dried (K2CO3) and concentrated to give N-methyl-3-phenyl-3-hydroxy-propyl-amine.
Quantity
2 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
Quantity
1.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0.4 g
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:3]1.[OH-].[Na+]>C(O)(=O)C.[Zn]>[CH3:1][NH:2][CH2:6][CH2:5][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3] |f:1.2|

Inputs

Step One
Name
Quantity
2 g
Type
reactant
Smiles
CN1OC(CC1)C1=CC=CC=C1
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)O
Name
Quantity
1.2 g
Type
catalyst
Smiles
[Zn]
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Three
Name
Quantity
0.4 g
Type
catalyst
Smiles
[Zn]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
heating
EXTRACTION
Type
EXTRACTION
Details
extracted with chloroform
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The extract is dried (K2CO3)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated

Outcomes

Product
Name
Type
product
Smiles
CNCCC(O)C1=CC=CC=C1

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
US05892117

Procedure details

2-Methyl-5-phenylisoxazolidine (2.0 g, 12.3 mmol) and Zn powder (1.2 g, 18.3 mmol) in 10 molar aqueous acetic acid are heated to 65°-70° C. for 4 hours. Additional Zn powder (0.4 g, 6.1 mmol) is added and heating is continued for one more hour. The reaction mixture is neutralized with sodium hydroxide and extracted with chloroform. The extract is dried (K2CO3) and concentrated to give N-methyl-3-phenyl-3-hydroxy-propyl-amine.
Quantity
2 g
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
Name
Quantity
1.2 g
Type
catalyst
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
0.4 g
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:3]1.[OH-].[Na+]>C(O)(=O)C.[Zn]>[CH3:1][NH:2][CH2:6][CH2:5][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3] |f:1.2|

Inputs

Step One
Name
Quantity
2 g
Type
reactant
Smiles
CN1OC(CC1)C1=CC=CC=C1
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)O
Name
Quantity
1.2 g
Type
catalyst
Smiles
[Zn]
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]
Step Three
Name
Quantity
0.4 g
Type
catalyst
Smiles
[Zn]

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
heating
EXTRACTION
Type
EXTRACTION
Details
extracted with chloroform
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The extract is dried (K2CO3)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated

Outcomes

Product
Name
Type
product
Smiles
CNCCC(O)C1=CC=CC=C1

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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