4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide

Base Information

• Chemical Name: 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide
• CAS No.: 27260-19-1
• Molecular Formula: C12H18 Cl N3 O2
• Molecular Weight: 271.747
• UNII: 44O5BC8E9J
• DSSTox Substance ID: DTXSID50181712
• Wikidata: Q83052333
• ChEMBL ID: CHEMBL616
• Mol file: 27260-19-1.mol

Synonyms:27260-19-1;N-Desethyl Metoclopramide;Desethylmetoclopramide;4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide;Deetilmetoclopramide;Deetilmetoclopramide [Italian];Deetilato metoclopramide;Monoethyl metoclopramide;Deetilato metoclopramide [Italian];BRN 2850460;4-Amino-5-chloro-N-(2-(ethylamino)ethyl)-o-anisamide;44O5BC8E9J;Benzamide, 4-amino-5-chloro-N-(2-(ethylamino)ethyl)-2-methoxy-;4-Amino-5-chloro-N-(2-ethylaminoethyl)-2-methoxybenzamide;4-Amino-5-chloro-N-(2-(ethylamino)ethyl)-2-methoxybenzamide;4-Amino-5-chloro-N-(2-etilaminoetil)-2-metossibenzamide [Italian];o-ANISAMIDE, 4-AMINO-5-CHLORO-N-(2-(ETHYLAMINO)ETHYL)-;C12H18ClN3O2;4-Amino-5-chloro-N-(2-etilaminoetil)-2-metossibenzamide;MDMCP;starbld0038633;CHEMBL616;UNII-44O5BC8E9J;N-(Ethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide;SCHEMBL15585981;DTXSID50181712;C12-H18-Cl-N3-O2;EX-A3519;METOCLOPRAMIDE METABOLITE M3;AKOS027192237;LS-20042;FT-0665989

Chemical Property of 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide

Chemical Property:

• Vapor Pressure: 4.41E-07mmHg at 25°C
• Melting Point: 142-143 °C
• Refractive Index: 1.5270 (estimate)
• Boiling Point: 414.5°C at 760 mmHg
• PKA: 14.28±0.46(Predicted)
• Flash Point: 204.5°C
• PSA: 79.87000
• Density: 1.2g/cm³
• LogP: 2.81700
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 271.1087545
• Heavy Atom Count: 18
• Complexity: 266

Purity/Quality:

99%, ^*data from raw suppliers

N-DesethylMetoclopramide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNCCNC(=O)C1=CC(=C(C=C1OC)N)Cl
• Uses: A novel Metoclopramide (M338685) metabolite in humans.

Technology Process of 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide

There total 4 articles about 4-amino-5-chloro-N-[2-(ethylamino)ethyl]-2-methoxybenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

N-ethylethane-1,2-diamine (110-72-5) + 4-amino-5-chloro-2-methoxybenzoic acid (7206-70-4) → N-deethyl-Metoclopramide (27260-19-1)

Guidance literature:

4-amino-5-chloro-2-methoxybenzoic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

N-ethylethane-1,2-diamine; In N,N-dimethyl-formamide; at 20 ℃; for 19h;

Reference yield:

metoclopramide (364-62-5) → N-deethyl-Metoclopramide (27260-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / Ambient temperature

2: aq. FeCl₂ / CH₂Cl₂ / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; iron(II) chloride; In dichloromethane;

DOI:10.1055/s-1985-31342

Reference yield:

metoclopramide N-oxide (171367-22-9) → N-deethyl-Metoclopramide (27260-19-1)

Guidance literature:

iron(II) chloride; In dichloromethane; Yield given; Ambient temperature;

DOI:10.1055/s-1985-31342

upstream raw materials:

metoclopramide N-oxide

metoclopramide

N-ethylethane-1,2-diamine

4-amino-5-chloro-2-methoxybenzoic acid

Downstream raw materials:

mPEG₂-N-metoclopramide

mPEG₃-N-metoclopramide

mPEG₁-N-metoclopramide

mPEG₄-N-metoclopramide

Refernces

• 1、 -. "OLIGOMER-CONTAINING BENZAMIDE-BASED COMPOUNDS". Paragraph 0166; 0167. . Retrieved 2014/04/03.