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molecular formula C14H22ClN3O2 B1676508 Metoclopramide CAS No. 364-62-5

Metoclopramide

Cat. No. B1676508
M. Wt: 299.79 g/mol
InChI Key: TTWJBBZEZQICBI-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04242507

Procedure details

2-Methoxy-4-amino-5-chlorobenzoic acid (1.0 g) and 1-methanesulfoyloxy-1,2,3-benzotriazole (1.07 g) are suspended into chloroform (15 ml) and therto is added dropwise triethylamine (0.7 ml) with stirring under ice-cooling to give a clear solution. To the solution is added 2-(diethylamino)ethylamine (0.6 g) at room temperature and the mixture is allowed to stand for 18 hours. The solvent is then distilled off and thereto are added water and 1 N aqueous sodium hydroxide. The resulting crystals are separated by filtration, washed with water and then dried to give N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide (0.9 g), melting point: 145°-146° C. The product is identified with an authentic sample by infrared spectrum.
Quantity
1 g
Type
reactant
Reaction Step One
[Compound]
Name
1-methanesulfoyloxy-1,2,3-benzotriazole
Quantity
1.07 g
Type
reactant
Reaction Step Two
Quantity
15 mL
Type
reactant
Reaction Step Three
Quantity
0.6 g
Type
reactant
Reaction Step Four
Quantity
0.7 mL
Type
solvent
Reaction Step Five

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH2:12])[C:9]([Cl:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(Cl)(Cl)Cl.[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][CH2:22][NH2:23])[CH3:19]>C(N(CC)CC)C>[CH2:18]([N:20]([CH2:24][CH3:25])[CH2:21][CH2:22][NH:23][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:13])[C:10]([NH2:12])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:19]

Inputs

Step One
Name
Quantity
1 g
Type
reactant
Smiles
COC1=C(C(=O)O)C=C(C(=C1)N)Cl
Step Two
Name
1-methanesulfoyloxy-1,2,3-benzotriazole
Quantity
1.07 g
Type
reactant
Smiles
Step Three
Name
Quantity
15 mL
Type
reactant
Smiles
C(Cl)(Cl)Cl
Step Four
Name
Quantity
0.6 g
Type
reactant
Smiles
C(C)N(CCN)CC
Step Five
Name
Quantity
0.7 mL
Type
solvent
Smiles
C(C)N(CC)CC

Conditions

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

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooling
CUSTOM
Type
CUSTOM
Details
to give a clear solution
DISTILLATION
Type
DISTILLATION
Details
The solvent is then distilled off
ADDITION
Type
ADDITION
Details
are added water and 1 N aqueous sodium hydroxide
CUSTOM
Type
CUSTOM
Details
The resulting crystals are separated by filtration
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
18 h
Name
Type
product
Smiles
C(C)N(CCNC(C1=C(C=C(C(=C1)Cl)N)OC)=O)CC
Measurements
Type Value Analysis
AMOUNT: MASS 0.9 g
YIELD: CALCULATEDPERCENTYIELD 60.5%

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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