Synthesis routes of Metoclopramide

Metoclopramide

Cat. No. B1676508

: 364-62-5

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.

Name

2-Methoxy-4-amino-5-chlorobenzoic acid

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

Name

chloroform

Quantity

15 mL

Type

reactant

Reaction Step Three

Name

2-(diethylamino)ethylamine

Quantity

0.6 g

Type

reactant

Reaction Step Four

Name

triethylamine

Quantity

0.7 mL

Type

solvent

Reaction Step Five

Name

N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide

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	2-Methoxy-4-amino-5-chlorobenzoic acid
Quantity	1 g
Type	reactant
Smiles	COC1=C(C(=O)O)C=C(C(=C1)N)Cl

Step Two

[Compound]

Name	1-methanesulfoyloxy-1,2,3-benzotriazole
Quantity	1.07 g
Type	reactant
Smiles

Step Three

Name	chloroform
Quantity	15 mL
Type	reactant
Smiles	C(Cl)(Cl)Cl

Step Four

Name	2-(diethylamino)ethylamine
Quantity	0.6 g
Type	reactant
Smiles	C(C)N(CCN)CC

Step Five

Name	triethylamine
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	N-(2-diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide
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

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.