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molecular formula C10H15NO B195923 3-(methylamino)-1-phenylpropan-1-ol CAS No. 42142-52-9

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

Cat. No. B195923
M. Wt: 165.23 g/mol
InChI Key: XXSDCGNHLFVSET-UHFFFAOYSA-N
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Patent
US05166437

Procedure details

An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six
[Compound]
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight
[Compound]
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten

Identifiers

REACTION_CXSMILES
[H][H].[C:3]1([CH:9]([OH:14])[CH2:10][CH2:11][NH:12][CH3:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.[Pt].[Pd].[Pd].[Pt].CS(C)=O.CN1CCCC1=O>[CH3:13][NH:12][CH2:11][CH2:10][CH:9]([O:14][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 |f:3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)OCC
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pt]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd].[Pt]
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN1C(CCC1)=O
Step Seven
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Nine
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
is formed

Outcomes

Product
Name
Type
product
Smiles
CNCCC(C1=CC=CC=C1)OC1=CC=C(C=C1)C(F)(F)F
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85%

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
US05166437

Procedure details

An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six
[Compound]
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight
[Compound]
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten

Identifiers

REACTION_CXSMILES
[H][H].[C:3]1([CH:9]([OH:14])[CH2:10][CH2:11][NH:12][CH3:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.[Pt].[Pd].[Pd].[Pt].CS(C)=O.CN1CCCC1=O>[CH3:13][NH:12][CH2:11][CH2:10][CH:9]([O:14][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 |f:3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)OCC
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pt]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd].[Pt]
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN1C(CCC1)=O
Step Seven
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Nine
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
is formed

Outcomes

Product
Name
Type
product
Smiles
CNCCC(C1=CC=CC=C1)OC1=CC=C(C=C1)C(F)(F)F
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85%

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
US05166437

Procedure details

An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
[Compound]
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Name
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
catalyst
Reaction Step Four
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six
[Compound]
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eight
[Compound]
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten

Identifiers

REACTION_CXSMILES
[H][H].[C:3]1([CH:9]([OH:14])[CH2:10][CH2:11][NH:12][CH3:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.[Pt].[Pd].[Pd].[Pt].CS(C)=O.CN1CCCC1=O>[CH3:13][NH:12][CH2:11][CH2:10][CH:9]([O:14][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1 |f:3.4,8.9|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Two
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[H][H]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)OCC
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pt]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd]
Name
Quantity
0 (± 1) mol
Type
catalyst
Smiles
[Pd].[Pt]
Step Five
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CN1C(CCC1)=O
Step Seven
Name
hydrochloride salt
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Name
( I )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Eight
Name
2-benzoyl-1-(N-benzyl-N-methyl)ethylamine
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Nine
Name
( II )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Ten
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O

Conditions

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

Workups

CUSTOM
Type
CUSTOM
Details
is formed

Outcomes

Product
Name
Type
product
Smiles
CNCCC(C1=CC=CC=C1)OC1=CC=C(C=C1)C(F)(F)F
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85%

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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