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molecular formula C14H18N2O2 B1678012 Nefiracetam CAS No. 77191-36-7

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.
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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.
Quantity
897 mg
Type
reactant
Reaction Step One
Quantity
2.13 g
Type
reactant
Reaction Step Two
Quantity
1.97 g
Type
reactant
Reaction Step Three
Name
Quantity
50 mL
Type
reactant
Reaction Step Four
Quantity
30 mL
Type
solvent
Reaction Step Five
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|

Inputs

Step One
Name
Quantity
897 mg
Type
reactant
Smiles
[NH2-].[Na+]
Step Two
Name
Quantity
2.13 g
Type
reactant
Smiles
N1C(CCC1)=O
Step Three
Name
Quantity
1.97 g
Type
reactant
Smiles
ClCC(=O)NC1=C(C=CC=C1C)C
Step Four
Name
Quantity
50 mL
Type
reactant
Smiles
O
Step Five
Name
Quantity
30 mL
Type
solvent
Smiles
COC(C)(C)C

Conditions

Stirring
Type
CUSTOM
Details
with stirring
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was slowly added
TEMPERATURE
Type
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
TEMPERATURE
Type
TEMPERATURE
Details
to cool
FILTRATION
Type
FILTRATION
Details
The thus formed crystals in the aqueous layer were collected by filtration
CUSTOM
Type
CUSTOM
Details
dried under reduced pressure

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)
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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