Eticlopride hydrochloride

Base Information

• Chemical Name: Eticlopride hydrochloride
• CAS No.: 97612-24-3
• Molecular Formula: C17H25 Cl N2 O3 . Cl H
• Molecular Weight: 377.311
• UNII: HJ2CAH4TZ1
• DSSTox Substance ID: DTXSID4045769
• Wikipedia: Eticlopride
• ChEMBL ID: CHEMBL1256917
• Mol file: 97612-24-3.mol

Synonyms:5-chloro-3-ethyl-N-((1-ethyl-2-pyrrolidinyl)methyl)-6-methoxysalicylamide;A 38503;eticlopride;FLB 131;FLB-131

Chemical Property of Eticlopride hydrochloride

Chemical Property:

• Vapor Pressure: 5E-08mmHg at 25°C
• Boiling Point: 430.8°Cat760mmHg
• Flash Point: 214.4°C
• PSA: 61.80000
• Density: g/cm³
• LogP: 3.96150
• Storage Temp.: Desiccate at RT
• Solubility.: H2O: soluble >10mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 376.1320481
• Heavy Atom Count: 24
• Complexity: 396

Purity/Quality:

98%,99%, ^*data from raw suppliers

EticloprideHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=CC(=C(C(=C1O)C(=O)NCC2CCCN2CC)OC)Cl.Cl
• Isomeric SMILES: CCC1=CC(=C(C(=C1O)C(=O)NC[C@@H]2CCCN2CC)OC)Cl.Cl
• Uses: Dopamine receptor antagonist S-(?)-Eticlopride hydrochloride has been used in astrocyte-neuron coculture and functional magnetic resonance imaging (fMRI) experiments.

Technology Process of Eticlopride hydrochloride

There total 3 articles about Eticlopride hydrochloride 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: 59.0%

(S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) + 3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid (101536-78-1) → Eticlopride hydrochloride (97612-24-3)

Guidance literature:

With thionyl chloride; In toluene; 21 grad C 1h then 50 grad C 0.5h;

Reference yield:

3-Chloro-5-ethyl-N-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-2,6-dimethoxy-benzamide (98575-96-3) → eticlopride (84226-12-0,151060-29-6,151123-04-5,97612-24-3) + Isoeticlopride (84226-13-1)

Guidance literature:

With hydrogenchloride; boron tribromide; In diethyl ether; dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jm00151a010

Reference yield:

2,6-dimethoxy-3-ethylbenzoic acid (96897-97-1) → Eticlopride hydrochloride (97612-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: HBr/HOAc / H₂O / 1 h / 35 °C

2: 83 percent / sulphuryl chloride / CHCl₃ / 4 h / Ambient temperature

3: 59 percent / thionyl chloride / toluene / 21 grad C 1h then 50 grad C 0.5h

With thionyl chloride; sulfuryl dichloride; hydrogen bromide; acetic acid; In chloroform; water; toluene;

upstream raw materials:

3-Chloro-5-ethyl-N-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-2,6-dimethoxy-benzamide

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

3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

2,6-dimethoxy-3-ethylbenzoic acid