Nefiracetam
Cat. No. B1678012
M. Wt: 246.30 g/mol
InChI Key: NGHTXZCKLWZPGK-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
Patent
US05461157
Procedure details
In 30 ml of t-butyl methyl ether was suspended 897 mg of sodium amide in a nitrogen stream, and 2.13 g of 2-pyrrolidinone was slowly added thereto dropwise, followed by refluxing for 2 hours. After allowing to cool, 1.97 g of 2-chloro-N-(2,6-dimethylphenyl)acetamide was added thereto, followed by refluxing for 2 hours. To the reaction mixture was added 50 ml of hot water of about 70° to 85° C., and the mixture was allowed to cool with stirring. The thus formed crystals in the aqueous layer were collected by filtration and dried under reduced pressure to obtain 2.19 g (89%) of the titled compound.
Name
Yield
89%
Identifiers
|
REACTION_CXSMILES
|
[NH2-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].Cl[CH2:10][C:11]([NH:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:21])=[O:12].O>COC(C)(C)C>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=1[NH:13][C:11](=[O:12])[CH2:10][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8] |f:0.1|
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Inputs
Step One
|
Name
|
|
|
Quantity
|
897 mg
|
|
Type
|
reactant
|
|
Smiles
|
[NH2-].[Na+]
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Step Two
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Name
|
|
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Quantity
|
2.13 g
|
|
Type
|
reactant
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|
Smiles
|
N1C(CCC1)=O
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Step Three
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Name
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|
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Quantity
|
1.97 g
|
|
Type
|
reactant
|
|
Smiles
|
ClCC(=O)NC1=C(C=CC=C1C)C
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Step Four
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Name
|
|
|
Quantity
|
50 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
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Step Five
|
Name
|
|
|
Quantity
|
30 mL
|
|
Type
|
solvent
|
|
Smiles
|
COC(C)(C)C
|
Conditions
Stirring
|
Type
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CUSTOM
|
|
Details
|
with stirring
|
|
Rate
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UNSPECIFIED
|
|
RPM
|
0
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Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
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Workups
ADDITION
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Type
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ADDITION
|
|
Details
|
was slowly added
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TEMPERATURE
|
Type
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TEMPERATURE
|
|
Details
|
by refluxing for 2 hours
|
|
Duration
|
2 h
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to cool
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
by refluxing for 2 hours
|
|
Duration
|
2 h
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TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to cool
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FILTRATION
|
Type
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FILTRATION
|
|
Details
|
The thus formed crystals in the aqueous layer were collected by filtration
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CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried under reduced pressure
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Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CC1=C(C(=CC=C1)C)NC(CN1C(CCC1)=O)=O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 2.19 g | |
| YIELD: PERCENTYIELD | 89% | |
| YIELD: CALCULATEDPERCENTYIELD | 89.2% |
Source
|
Source
|
Open Reaction Database (ORD) |
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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. |
