N-(2-(N-Methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine

Base Information

• Chemical Name: N-(2-(N-Methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine
• CAS No.: 115199-84-3
• Molecular Formula: C21H24 Cl2 N2 O . Cl H
• Molecular Weight: 427.801
• UNII: CT5E310AJL
• DSSTox Substance ID: DTXSID60921646
• Wikipedia: ICI-199,441
• Mol file: 115199-84-3.mol

Synonyms:ICI 199,441;ICI 199441;ICI-199441;N-(2-(N-methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine

Chemical Property of N-(2-(N-Methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine

Chemical Property:

• Vapor Pressure: 1.97E-11mmHg at 25°C
• Boiling Point: 532.8°Cat760mmHg
• Flash Point: 276°C
• PSA: 23.55000
• Density: g/cm³
• LogP: 5.57130
• Storage Temp.: Store at RT
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 426.103247
• Heavy Atom Count: 27
• Complexity: 449

Purity/Quality:

98%Min ^*data from raw suppliers

ICI199441 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(CN1CCCC1)C2=CC=CC=C2)C(=O)CC3=CC(=C(C=C3)Cl)Cl.Cl
• Isomeric SMILES: CN([C@H](CN1CCCC1)C2=CC=CC=C2)C(=O)CC3=CC(=C(C=C3)Cl)Cl.Cl
• Uses: Opioid agonists exert a broad range of effects on the immune system ranging from inflammatory response modulation to opioid and chemokine receptor expression. ICI 199441 is a selective κ-opioid agonist with analgesic properties.

Technology Process of N-(2-(N-Methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine

There total 4 articles about N-(2-(N-Methyl-3,4-dichlorophenylacetamido)-2-phenylethyl)pyrrolidine 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:

((S)-2-Oxo-1-phenyl-2-pyrrolidin-1-yl-ethyl)-carbamic acid methyl ester (130013-63-7) → ICI 199441 hydrochloride (115199-84-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LAH / tetrahydrofuran

2: CH₂Cl₂

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00105a027

Reference yield:

(1S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine (116508-51-1) + 2-(3,4-dichlorophenyl)acetyl chloride (6831-55-6) → ICI 199441 hydrochloride (115199-84-3)

Guidance literature:

In dichloromethane; Yield given;

DOI:10.1021/jm00105a027

Reference yield:

(S)-2-((methoxycarbonyl)amino)-2-phenylacetic acid (60725-19-1) → ICI 199441 hydrochloride (115199-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / 1-hydroxybenzotriazole (HOBT), DCC / CH₂Cl₂

2: LAH / tetrahydrofuran

3: CH₂Cl₂

With lithium aluminium tetrahydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00105a027

upstream raw materials:

(1S)-N-methyl-1-phenyl-2-(pyrrolidin-1-yl)ethanamine

2-(3,4-dichlorophenyl)acetyl chloride

(S)-2-((methoxycarbonyl)amino)-2-phenylacetic acid

((S)-2-Oxo-1-phenyl-2-pyrrolidin-1-yl-ethyl)-carbamic acid methyl ester

Refernces

• 1、 Costello, Gerard F.,James, Roger,Shaw, John S.,Slater, Anthony M.,Stutchbury, Neil C. J.. "2-(3,4-Dichlorophenyl)-N-methyl-N-acetamides: The Use of Conformational Analysis in the Development of a Novel Series of Potent Opioid κ Agonists". . p. 181 - 189. Retrieved 2007/10/02.