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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 N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine of formula (I), ##STR5## or a pharmaceutically acceptable acid addition salt thereof, the said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR6## to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III), ##STR7## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR8## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of a potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
( IV )
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 Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[C:1]1([CH:7]([OH:12])[CH2:8][CH2:9][NH:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.CN1CCCC1=O.CC(C)([O-])C.[K+]>CS(C)=O>[CH3:11][NH:10][CH2:9][CH2:8][CH:7]([O:12][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 |f:3.4|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Three
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

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 N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine of formula (I), ##STR5## or a pharmaceutically acceptable acid addition salt thereof, the said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR6## to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III), ##STR7## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR8## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of a potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
( IV )
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 Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[C:1]1([CH:7]([OH:12])[CH2:8][CH2:9][NH:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.CN1CCCC1=O.CC(C)([O-])C.[K+]>CS(C)=O>[CH3:11][NH:10][CH2:9][CH2:8][CH:7]([O:12][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 |f:3.4|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Three
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

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 N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine of formula (I), ##STR5## or a pharmaceutically acceptable acid addition salt thereof, the said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR6## to obtain 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III), ##STR7## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR8## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of a potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
( IV )
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 Five
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Six

Identifiers

REACTION_CXSMILES
[C:1]1([CH:7]([OH:12])[CH2:8][CH2:9][NH:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.CN1CCCC1=O.CC(C)([O-])C.[K+]>CS(C)=O>[CH3:11][NH:10][CH2:9][CH2:8][CH:7]([O:12][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 |f:3.4|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1(=CC=CC=C1)C(CCNC)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC=C(C=C1)C(F)(F)F
Step Three
Name
( IV )
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CN1C(CCC1)=O
Step Five
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C)([O-])C.[K+]
Step Six
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CS(=O)C

Conditions

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

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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