Mirfentanil

Base Information

• Chemical Name: Mirfentanil
• CAS No.: 117523-47-4
• Molecular Formula: C22H24 N4 O2
• Molecular Weight: 376.458
• UNII: Q2U943H24P
• DSSTox Substance ID: DTXSID10151799
• Nikkaji Number: J386.533I
• Wikipedia: Mirfentanil
• Wikidata: Q6873205
• NCI Thesaurus Code: C174864
• Metabolomics Workbench ID: 152211
• ChEMBL ID: CHEMBL161084
• Mol file: 117523-47-4.mol

Synonyms:mirfentanil;MS 32;MS-32;MS32;N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide;NIH 10647;NIH-10647

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Mirfentanil

Chemical Property:

• Vapor Pressure: 1.17E-11mmHg at 25°C
• Boiling Point: 538.3°Cat760mmHg
• Flash Point: 279.3°C
• PSA: 62.47000
• Density: 1.222g/cm³
• LogP: 3.36140
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 376.18992602
• Heavy Atom Count: 28
• Complexity: 489

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1N(C2=NC=CN=C2)C(=O)C3=CC=CO3)CCC4=CC=CC=C4
• Uses: Analgesic.

Technology Process of Mirfentanil

There total 5 articles about Mirfentanil 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: 54.0%

2-furancarbonyl chloride (527-69-5) + 1-phenethyl-4-piperidine (117523-88-3) → N-(1-phenethylpiperidin-4-yl)-N-(pyrazin-2-yl)furan-2-carboxamide (117523-47-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/cphc.202100165

Reference yield:

4-amino-1-(2-phenylethyl)-piperidine (51448-56-7) → N-(1-phenethylpiperidin-4-yl)-N-(pyrazin-2-yl)furan-2-carboxamide (117523-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / Cu powder / 6 h / 170 - 180 °C

2: 45 percent / Et₃N / CHCl₃ / 0.5 h / Ambient temperature

With copper; triethylamine; In chloroform;

DOI:10.1021/jm00123a028

Reference yield:

1-(2-phenylethyl)-4-piperidinone (39742-60-4) → N-(1-phenethylpiperidin-4-yl)-N-(pyrazin-2-yl)furan-2-carboxamide (117523-47-4)

Guidance literature:

Multi-step reaction with 5 steps

1: hydroxylamine hydrochloride; potassium hydroxide / methanol; water / 24 h / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux

3: sodium hydroxide / water / pH 12

4: copper / 6 h / 180 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

With lithium aluminium tetrahydride; hydroxylamine hydrochloride; copper; N-ethyl-N,N-diisopropylamine; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/cphc.202100165

upstream raw materials:

2-furancarbonyl chloride

1-phenethyl-4-piperidine

1-phenethylpiperidin-4-one oxime

4-amino-1-(2-phenylethyl)-piperidine

Refernces

• 1、 Bagley,Wynn,Rudo,Doorley,Spencer,Spaulding. "New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties". . p. 663 - 671. Retrieved 2007/10/02.