4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE Chemical Properties

Boiling point:

120-123 °C(Press: 0.3 Torr)

Density 

1.021±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

9.29±0.10(Predicted)

form 

Oil

color 

Colourless

InChI

InChI=1S/C11H18N2O/c1-13(2)7-8-14-11-5-3-10(9-12)4-6-11/h3-6H,7-9,12H2,1-2H3

InChIKey

OBHPRQNPNGQGCK-UHFFFAOYSA-N

SMILES

C1(CN)=CC=C(OCCN(C)C)C=C1

LogP

0.860 (est)

CAS DataBase Reference

20059-73-8(CAS DataBase Reference)

Safety Information

Risk Statements 

43

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

2921490090

4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE Usage And Synthesis

Uses

4-[2-(Dimethylamino)ethoxy]benzylamine is an impurity of Itopride (HCl: I931500), a gastroprokinetic benzamide derivative that is used to treat patients with dyspepsia.

Definition

ChEBI: 4-[2-(Dimethylamino)ethoxy]benzylamine is an aromatic amine.

Synthesis

General procedure for the synthesis of 4-[2-(dimethylamino)ethoxy]benzylamine from 4-(2-(dimethylamino)ethoxy)benzenecarboxaldehyde: 27 kg of 80% acetic acid was added to the reactor, followed by 5.3 kg of hydroxylamine hydrochloride. The mixture was cooled to 0-5 °C. A solution of acetic acid containing 13.5 kg of 100% 4-(2-dimethylaminoethoxy)benzaldehyde was added to the above cooled mixture. The reaction mixture was kept at 0-5°C for at least 2 hours. Upon completion of the reaction, 10.8 kg of powdered zinc was added in batches and the temperature was controlled not to exceed 50°C. The mixture was stirred at 45-50°C for at least 5 hours and then heated to 65-70°C and kept for at least 2 hours. Upon completion of the reaction, the reaction mixture was distilled to give a thick but stirrable residue. To the residue was added 20.3 kg of deionized water and the mixture was cooled to 20-30 °C. 54 kg of 30% ammonia was added slowly and dropwise to ensure that the pH of the reaction mixture was above 9.5. After stirring for at least 10 minutes at 20-30 °C, the reaction mixture was extracted with 40.5 kg of dichloromethane at 20-25 °C. The reaction mixture was then extracted with aqueous phase of 30% ammonia. The organic phase was separated and the aqueous phase was then subjected to a second extraction with 27 kg of dichloromethane, stirring for at least 5 minutes before combining the organic phases. The solvent was removed by distillation to give an oily residue. To the residue was added 54 kg of sec-butanol and 20.3 kg of N,N-dimethylformamide to give a solution containing 11.5 kg of 4-(2-dimethylaminoethoxy)benzylamine in 84.7% yield.

References

[1] Patent: WO2006/51079, 2006, A1. Location in patent: Page/Page column 5-6
[2] Patent: US2879293, 1957,
[3] Organic Process Research and Development, 2013, vol. 17, # 7, p. 981 - 984
[4] Patent: KR101819771, 2018, B1. Location in patent: Paragraph 0023; 0045-0052

4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE(20059-73-8)Related Product Information

• 3,4-Dimethoxybenzoic acid
• 4-[2-(DIMETHYLAMINO)ETHOXY]BENZONITRILE
• Itopride N-Oxide
• ETHYL 3,4-DIMETHOXYBENZOATE
• 3,4-DIMETHOXYBENZOYL CHLORIDE
• N,N-Dimethyl-2-(p-tolyloxy)ethanamine
• [4-[2-(DIMETHYLAMINO)ETHOXY]PHENYL]METHANOL
• N-Desmethyl Itopride Hydrochloride
• Itopride Impurity C
• Itopride Impurity A
• 4-Hydroxybenzylamine
• Itopride Impurity 1
• 2-(p-tolyloxy)-N,N-dimethylethanamine hydrochloride
• Benzaldehyde, 4-[2-(diMethylaMino)ethoxy]-, oxiMe
• Itopride Impurity B
• 3,4-Dimethoxybenzyl alcohol
• 2-Dimethylaminoethanol
• N-[[4-[2-[bis(trideuteriomethyl)amino]ethoxy]phenyl]methyl]-3,4-dimethoxybenzamide:hydrochloride