(S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide

Base Information

• Chemical Name: (S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide
• CAS No.: 84226-04-0
• Molecular Formula: C15H22 N2 O3
• Molecular Weight: 278.351
• DSSTox Substance ID: DTXSID40449797
• Nikkaji Number: J486.500F
• Wikidata: Q82269314
• ChEMBL ID: CHEMBL8945
• Mol file: 84226-04-0.mol

Synonyms:84226-04-0;N-[[(2S)-1-Ethylpyrrolidin-2-yl]methyl]-2-hydroxy-6-methoxybenzamide;CHEMBL8945;(S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide;S-(-)-Bzm;SCHEMBL3805660;DTXSID40449797;BDBM50012964;BENZAMIDE, N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-2-HYDROXY-6-METHOXY-, (S)-;N-(1-Ethyl-pyrrolidin-2-ylmethyl)-2-hydroxy-6-methoxy-benzamide;2-Hydroxy-6-methoxy-N-[[(2S)-1-ethylpyrrolidin-2alpha-yl]methyl]benzamide;N-(1-Ethyl-pyrrolidin-2-ylmethyl)-2-hydroxy-6-methoxy-benzamide (BZM)

Chemical Property of (S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide

Chemical Property:

• Appearance/Colour: pale yellow semisolid
• Boiling Point: 443 °C at 760 mmHg
• Flash Point: 221.7 °C
• PSA: 61.80000
• Density: 1.133 g/cm³
• LogP: 1.94370
• Storage Temp.: −20°C
• Solubility.: DMSO: 14.6 mg/mL
• Water Solubility.: at 25 deg C (mg/L): 400.5
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 278.16304257
• Heavy Atom Count: 20
• Complexity: 324

Purity/Quality:

S-(-)-BZM 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: WGK Germany : 3:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C=CC=C2OC)O
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C=CC=C2OC)O
• Uses: A precursor to radio-iodinated S(–)-IBZM, a D2 dopamine receptor ligand.

Technology Process of (S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-methoxybenzamide

There total 4 articles about (S)-N-((1-Ethylpyrrolidin-2-yl)methyl)-2-hydroxy-6-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: 76.0%

2-hydroxy-6-methoxybenzoic acid (3147-64-6) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → (-)-BZM (84226-04-0)

Guidance literature:

2-hydroxy-6-methoxybenzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.1h;

(S)-2-(Aminomethyl)-1-ethylpyrrolidine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/acs.orglett.5b02345

Reference yield: 69.7%

(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide (96947-76-1) → (-)-BZM (84226-04-0)

Guidance literature:

(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide; With hydrogenchloride; In methanol; water;

With boron tribromide; In dichloromethane; at 20 ℃; for 4h;

Reference yield:

2-6-dimethoxybenzoic acid (1466-76-8) → (-)-BZM (84226-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂, DMF / CHCl₃ / 2 h / Heating

2: CHCl₃ / 24 h / Ambient temperature

3: 1.) HCl gas, 2.) BBr₃ / 1.) CHCl₃, 15 min, 2.) CH₂Cl₂, room temperature, 1.5 h

With hydrogenchloride; thionyl chloride; boron tribromide; N,N-dimethyl-formamide; In chloroform;

DOI:10.1021/jm00400a027

upstream raw materials:

(S)-(-)-N-<(ethyl-2-pyrrolidinyl)methyl>-2,6-dimethoxybenzamide

2-6-dimethoxybenzoic acid

2,6-dimethoxybenzoyl chloride

2-hydroxy-6-methoxybenzoic acid

Downstream raw materials:

[123I]-IBZM

(S)-(-)-2-hydroxy-6-methoxy-N-<(1-ethyl-2-pyrrolidinyl)methyl>benzamide (+)-tartrate

FLA 797

(-)-FLA 908