Remoxipride

Base Information

• Chemical Name: Remoxipride
• CAS No.: 80125-14-0
• Molecular Formula: C16H23BrN2O3
• Molecular Weight: 371.274
• UNII: 0223RD59PE
• DSSTox Substance ID: DTXSID6045668
• Nikkaji Number: J138.394I
• Wikipedia: Remoxipride
• Wikidata: Q1169059
• NCI Thesaurus Code: C73312
• Pharos Ligand ID: 49823XAFRQQC
• Metabolomics Workbench ID: 42770
• ChEMBL ID: CHEMBL22242
• Mol file: 80125-14-0.mol

Synonyms:(S)-3-Bromo-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dimethoxybenzamide;Anhydrous, Remoxipride Hydrochloride;FLA-731;FLA731;Hydrochloride Anhydrous, Remoxipride;Hydrochloride, Remoxipride;Monohydrochloride Monohydrate, Remoxipride;Monohydrochloride, Remoxipride;Remoxipride;Remoxipride Hydrochloride;Remoxipride Hydrochloride Anhydrous;Remoxipride Monohydrochloride;Remoxipride Monohydrochloride Monohydrate;Remoxipride Monohydrochloride, (R)-Isomer;Remoxipride, (R)-Isomer

Chemical Property of Remoxipride

Chemical Property:

• Vapor Pressure: 6.17E-08mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 439.9°C at 760 mmHg
• PKA: pKa 8.9 (Uncertain)
• Flash Point: 219.8°C
• PSA: 50.80000
• Density: 1.292 g/cm³
• LogP: 3.00920
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 370.08921
• Heavy Atom Count: 22
• Complexity: 369

Purity/Quality:

98%min ^*data from raw suppliers

Remoxipride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C=CC(=C2OC)Br)OC
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2OC)Br)OC
• Uses: Antipsychotic.

Technology Process of Remoxipride

There total 4 articles about Remoxipride 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:

2-6-dimethoxybenzoic acid (1466-76-8) → remoxipride (80125-14-0,82935-42-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Br₂ / CHCl₃; dioxane / 2 h / Ambient temperature

2: SOCl₂ / 0.5 h / Heating

3: 10N aq. NaOH / CHCl₃ / 0.17 h / Heating

With sodium hydroxide; thionyl chloride; bromine; In 1,4-dioxane; chloroform;

DOI:10.1021/jm00353a003

Reference yield:

3-bromo-2,6-dimethoxybenzoic acid (73219-89-3) → remoxipride (80125-14-0,82935-42-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 0.5 h / Heating

2: 10N aq. NaOH / CHCl₃ / 0.17 h / Heating

With sodium hydroxide; thionyl chloride; In chloroform;

DOI:10.1021/jm00353a003

Reference yield:

5-bromo-2,6-dimethoxybenzoic acid chloride (84225-91-2) + di-D-(-)-tartrate salt of (S)-2-aminomethyl-1-ethylpyrrolidine (84277-13-4) → remoxipride (80125-14-0,82935-42-0)

Guidance literature:

With sodium hydroxide; In chloroform; for 0.166667h; Yield given; Heating;

DOI:10.1021/jm00353a003

upstream raw materials:

5-bromo-2,6-dimethoxybenzoic acid chloride

di-D-(-)-tartrate salt of (S)-2-aminomethyl-1-ethylpyrrolidine

3-bromo-2,6-dimethoxybenzoic acid

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

Refernces

• 1、 Florvall, Lennart,Oegren, Sven-Ove. "Potential Neuroleptic Agents. 2,6-Dialkoxybenzamide Derivatives with Potent Dopamine Receptor Blocking Activities". . p. 1280 - 1286. Retrieved 2007/10/02.