Sunifiram

Base Information

• Chemical Name: Sunifiram
• CAS No.: 314728-85-3
• Molecular Formula: C14H18N2O2
• Molecular Weight: 246.30
• UNII: 66924E735K
• ChEMBL ID: CHEMBL309176
• DSSTox Substance ID: DTXSID10400996
• Nikkaji Number: J1.445.767D
• Wikidata: Q6590525
• Wikipedia: Sunifiram
• Mol file: 314728-85-3.mol

Synonyms:DM 235;DM-235;DM235 cpd;sunifiram

Chemical Property of Sunifiram

Chemical Property:

• Boiling Point: 442.0±38.0 °C(Predicted)
• PKA: 0.08±0.70(Predicted)
• PSA: 40.62000
• Density: 1.154±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 1.25680
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble24mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 246.136827821
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

99%, ^*data from raw suppliers

Sunifiram ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)N1CCN(CC1)C(=O)C2=CC=CC=C2
• Description: Sunifiram (DM-235) is a synthetic derivative of piracetam, although due to breaking the pyrrolidone backbone it is no longer in the racetam class of drugs (yet by being derived from them, it is still commonly associated with this class).Sunifiram has mechanisms similar to nefiracetam in the hippocampus, and similar to that drug sunifiram shows anti-amnesiac properties and is potentially a cognitive enhancer. Its anti-amnesiac activity is several orders of magnitude greater than piracetam on a per weight basis, and preliminary evidence suggest it has a similarly low toxicity profile.
• Uses: Sunifiram is a potent nootropic agent.

Technology Process of Sunifiram

There total 4 articles about Sunifiram 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: 93.0%

1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one (54264-50-5) + N-Benzoylpiperazine (13754-38-6) → Sunifiram (314728-85-3)

Guidance literature:

In butan-1-ol; at 60 ℃;

DOI:10.1080/14756366.2022.2068147

Reference yield: 87.0%

propionyl chloride (79-03-8) + N-Benzoylpiperazine (13754-38-6) → Sunifiram (314728-85-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jacs.9b03138

Reference yield:

1-(4-benzyl-piperazin-1-yl)-propan-1-one (314728-80-8) → Sunifiram (314728-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 2430.66 Torr

2: NEt₃ / acetonitrile / 2 h / 20 °C

With hydrogen; triethylamine; 10percent Pd/C; In ethanol; acetonitrile;

DOI:10.1021/jm000972h

upstream raw materials:

1-(piperazin-1-yl)propan-1-one

benzoyl chloride

1-(4-benzyl-piperazin-1-yl)-propan-1-one

propionyl chloride

Refernces

• 1、 Yang, Lichen,Uemura, Nao,Nakao, Yoshiaki. "Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst". supporting information. p. 7972 - 7979. Retrieved 2019/05/22.