Patent
US08080536B2
Procedure details
A solution of bis(2-chloroethyl)phosphoramidic dichloride (10 mmol) in ethyl acetate (100 mL) is added dropwise to a solution of commercial 3 methylamino-1-phenyl-1-propanol (10 mmol) and triethylamine (20 mmol) in ethyl acetate (100 mL) at rt. After stirring at rt for 3 days, the salts are filtered off and the combined filtrates are concentrated under vacuum. The crude product is purified by column chromatography on silica.
Name
methylamino-1-phenyl-1-propanol
Quantity
10 mmol
Type
reactant
Reaction Step One
Name
Identifiers
|
REACTION_CXSMILES
|
[Cl:1][CH2:2][CH2:3][N:4]([CH2:9][CH2:10][Cl:11])[P:5](Cl)(Cl)=[O:6].CN[C:14]([C:18]1[CH:23]=CC=CC=1)([OH:17])CC.C([N:26](CC)CC)C>C(OCC)(=O)C>[CH2:18]1[CH2:14][O:17][P:5]([N:4]([CH2:9][CH2:10][Cl:11])[CH2:3][CH2:2][Cl:1])(=[O:6])[NH:26][CH2:23]1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
10 mmol
|
|
Type
|
reactant
|
|
Smiles
|
ClCCN(P(=O)(Cl)Cl)CCCl
|
|
Name
|
methylamino-1-phenyl-1-propanol
|
|
Quantity
|
10 mmol
|
|
Type
|
reactant
|
|
Smiles
|
CNC(CC)(O)C1=CC=CC=C1
|
|
Name
|
|
|
Quantity
|
20 mmol
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N(CC)CC
|
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)(=O)OCC
|
Conditions
Temperature
|
Control Type
|
AMBIENT
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
After stirring at rt for 3 days
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
the salts are filtered off
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
the combined filtrates are concentrated under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The crude product is purified by column chromatography on silica
|
Outcomes
Product
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. |
