S-(+)-O-Desmethylraclopride hydrobromide

Base Information

• Chemical Name: S-(+)-O-Desmethylraclopride hydrobromide
• CAS No.: 113310-88-6
• Molecular Formula: BrH*C₁₄H₁₈Cl₂N₂O₃
• Molecular Weight: 414.126
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00585125
• Mol file: 113310-88-6.mol

Synonyms:113310-88-6;S-(+)-O-Desmethylraclopride hydrobromide;(S)-3,5-Dichloro-N-((1-ethylpyrrolidin-2-yl)methyl)-2,6-dihydroxybenzamide hydrobromide;3,5-dichloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dihydroxybenzamide;hydrobromide;(S)-3,5-DICHLORO-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-2,6-DIHYDROXY-BENZAMIDE HYDROBROMIDE;DTXSID00585125;3,5-DICHLORO-N-{[(2S)-1-ETHYLPYRROLIDIN-2-YL]METHYL}-2,6-DIHYDROXYBENZAMIDE HYDROBROMIDE;J-002939;S-(+)-O-Desmethylraclopride hydrobromide, solid, >=98% (HPLC);(s)-3,5-dichloro-2,6-dihydroxy-N-[(1-ethyl-2-pyrrolidinyl)-methyl]benzamide hydrobromide;3,5-Dichloro-N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2,6-dihydroxybenzamide--hydrogen bromide (1/1)

Chemical Property of S-(+)-O-Desmethylraclopride hydrobromide

Chemical Property:

• PSA: 72.80000
• LogP: 3.90560
• Solubility.: H2O: 10 mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 411.99561
• Heavy Atom Count: 22
• Complexity: 358

Purity/Quality:

99.3% ^*data from raw suppliers

S-(+)-O-Desmethylraclopride hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C(=CC(=C2O)Cl)Cl)O.Br
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C(=CC(=C2O)Cl)Cl)O.Br
• Uses: S-(+)-O-Desmethylraclopride Hydrobromide is used for the improved synthesis of [11C]-raclopride, a PET dopamine D2 receptors radioligand.

Technology Process of S-(+)-O-Desmethylraclopride hydrobromide

There total 6 articles about S-(+)-O-Desmethylraclopride hydrobromide 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: 81.0%

raclopride hydrochloride (98527-32-3) → (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide hydrobromide (113310-88-6)

Guidance literature:

With hydrogen bromide; acetic acid;

Reference yield: 54.0%

raclopride (84225-95-6) → (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide hydrobromide (113310-88-6)

Guidance literature:

With hydrogen bromide; In acetic acid; at 60 ℃; for 2h;

DOI:10.1002/(SICI)1099-1344(199912)42:12<1183::AID-JLCR274>3.0.CO;2-Z

Reference yield:

2,6-dimethoxy-3,5-dichlorobenzoic acid (73219-91-7) → (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide hydrobromide (113310-88-6)

Guidance literature:

Multi-step reaction with 4 steps

1: SOCl₂ / toluene; dimethylformamide / 2 h / 60 °C

2: 3.13 g / CH₂Cl₂ / 20 °C

3: 71 percent / BBr₃ / CH₂Cl₂ / -20 - 20 °C

4: 54 percent / HBr / acetic acid / 2 h / 60 °C

With thionyl chloride; hydrogen bromide; boron tribromide; In dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1081/SCC-120034174

upstream raw materials:

raclopride hydrochloride

raclopride

2,6-dimethoxy-3,5-dichlorobenzoic acid

3,5-dichloro-2,6-dimethoxybenzoic acid chloride

Refernces

• 1、 Langer, Oliver,Nagren, Kjell,Dolle, Frederic,Lundkvist, Camilla,Sandell, Johan,Swahn, Carl-Gunnar,Vaufrey, Francoise,Crouzel, Christian,Maziere, Bernard,Halldin, Christer. "Precursor synthesis and radiolabelling of the dopamine D2 receptor ligand [11C]raclopride from [11C]methyl triflate". . p. 1183 - 1193. Retrieved 1999.