trans-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide

Base Information

• Chemical Name: trans-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide
• CAS No.: 67198-13-4
• Deprecated CAS: 83913-05-7
• Molecular Formula: C19H26Cl2N2O
• Molecular Weight: 369.334
• DSSTox Substance ID: DTXSID50849401
• Nikkaji Number: J253.144E
• Wikipedia: U-50488
• Wikidata: Q7862881
• Pharos Ligand ID: KX9ZWZDTWB3M
• Metabolomics Workbench ID: 66389
• ChEMBL ID: CHEMBL441765
• Mol file: 67198-13-4.mol

Synonyms:3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Mesylate, (trans)-(+)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Mesylate, (trans)-(+-)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Monohydrochloride, (trans)-(+-)-Isomer,;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Monomethanesulfonate, (trans)-(+)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Monomethanesulfonate, (trans)-(+-)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide Monomethanesulfonate, (trans)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide, (1R-cis)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide, (1S-cis)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide, (trans)-(+-)-Isomer;3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide, (trans)-(-)-Isomer;Benzeneacetamide, 3,4-dichloro-N-methyl-N-(2-(1-pyrrolidinyl)cyclohexyl)-, (trans)-Isomer;trans-3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide;trans-3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide Hydrochloride;U 50,488H;U 50488;U 50488H;U-50,488H;U-50488;U-50488H;U50,488H;U50488;U50488H

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Chemical Property of trans-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide

Chemical Property:

• Vapor Pressure: 5.35E-10mmHg at 25°C
• Melting Point: 204-208℃
• Boiling Point: 496.6°Cat760mmHg
• Flash Point: 254.1°C
• PSA: 86.30000
• Density: 1.23g/cm³
• LogP: 4.92400
• Storage Temp.: Desiccate at RT
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 368.1422188
• Heavy Atom Count: 24
• Complexity: 428

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1CCCCC1N2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl
• Isomeric SMILES: CN([C@@H]1CCCC[C@H]1N2CCCC2)C(=O)CC3=CC(=C(C=C3)Cl)Cl
• Recent EU Clinical Trials: OASIS: A Phase 2/3 Randomized, Double-blind, Placebo-controlled Study of the Safety and Efficacy of Talactoferrin Alfa in Patients with Severe Sepsis
• Uses: U 50488 is a selective κ-opioid agonist with analgesic, diuretic, and antitussive properties. κ-opioid agonists are useful compounds to elucidate the functions of κ-receptors in the central nervous system.

Technology Process of trans-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide

There total 10 articles about trans-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-benzeneacetamide 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: 100.0%

3,4-dichlorophenyl acetic acid (5807-30-7) + (+/-)-cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine (67198-34-9,67198-53-2,67347-43-7,99239-39-1,116301-06-5,121843-49-0,121843-50-3,121843-51-4,142434-12-6) → cis U 50488 (67198-13-4,67198-17-8,67198-19-0,83913-05-7,116301-05-4,121843-48-9,121843-52-5,121843-54-7,149341-39-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1021/jm00128a050

Reference yield:

3,4-dichlorophenyl acetic acid (5807-30-7) + trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine (67198-34-9,67198-53-2,67347-43-7,99239-39-1,116301-06-5,121843-49-0,121843-50-3,121843-51-4,142434-12-6) → trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidynyl)-cyclohexyl]benzeneacetamide (67198-13-4,67198-17-8,67198-19-0,83913-05-7,116301-05-4,121843-48-9,121843-52-5,121843-54-7,149341-39-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201100278

Reference yield:

trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine (67198-34-9,67198-53-2,67347-43-7,99239-39-1,116301-06-5,121843-49-0,121843-50-3,121843-51-4,142434-12-6) + 2-(3,4-dichlorophenyl)acetyl chloride (6831-55-6) → trans-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidynyl)-cyclohexyl]benzeneacetamide (67198-13-4,67198-17-8,67198-19-0,83913-05-7,116301-05-4,121843-48-9,121843-52-5,121843-54-7,149341-39-9)

Guidance literature:

With 1,1'-carbonyldiimidazole; Multistep reaction; 1.) THF, 2.) THF;

DOI:10.1021/jm00352a005

upstream raw materials:

trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine

2-(3,4-dichlorophenyl)acetyl chloride

(+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol

3,4-dichlorophenyl acetic acid

Downstream raw materials:

U 50488 hydrochloride

(1R,2R)-(-)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine