4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide

Base Information

• Chemical Name: 4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide
• CAS No.: 156727-74-1
• Molecular Formula: C28H39 N3 O2
• Molecular Weight: 449.637
• NSC Number: 707484
• UNII: L842QB22SW
• DSSTox Substance ID: DTXSID6045662
• Nikkaji Number: J601.902A
• Wikipedia: SNC-80
• Wikidata: Q7391803
• Pharos Ligand ID: 9DBFN73R7QT3
• ChEMBL ID: CHEMBL13470
• Mol file: 156727-74-1.mol

Synonyms:4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide;SNC 80;SNC-80;SNC80

Chemical Property of 4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide

Chemical Property:

• Vapor Pressure: 8.83E-13mmHg at 25°C
• Melting Point: 122-123°C
• Boiling Point: 564.8°Cat760mmHg
• PKA: 7.29±0.10(Predicted)
• Flash Point: 295.4°C
• PSA: 36.02000
• Density: 1.04g/cm³
• LogP: 4.72300
• Storage Temp.: Store at RT
• Solubility.: DMSO: soluble
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 449.30422750
• Heavy Atom Count: 33
• Complexity: 614

Purity/Quality:

98%,99%, ^*data from raw suppliers

SNC80 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1=CC=C(C=C1)C(C2=CC(=CC=C2)OC)N3CC(N(CC3C)CC=C)C
• Isomeric SMILES: CCN(CC)C(=O)C1=CC=C(C=C1)[C@H](C2=CC(=CC=C2)OC)N3C[C@H](N(C[C@@H]3C)CC=C)C
• Description: SNC 80 is a selective nonpeptide agonist of the δ-opioid receptor (Ki = 0.18 nM, IC50 = 2.73 nM) that is over 2,000-fold less effective at the μ-opioid receptor. It effectively activates μ/δ receptor heteromers (EC50 = 52.8 nM) but not κ/δ or μ/κ heteromers. SNC 80 has antinociceptive as well as pro-convulsant effects in vivo.
• Uses: A highly selective and potent non-peptide -agonist, 2000-fold selective over u-receptors Rats were administered SNC80 to study the role of nitric oxide synthase in peripheral antinociception mechanism.5

Technology Process of 4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide

There total 16 articles about 4-(alpha-(4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide 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: 35.0%

N,N-diethyl-4-formylbenzamide (58287-77-7) + (3-methoxyphenyl)magnesium bromide (36282-40-3) + (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine (155836-78-5) → (+)-4-[(αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide (156727-74-1)

Guidance literature:

N,N-diethyl-4-formylbenzamide; (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine; With 1,2,3-Benzotriazole; In toluene; for 2 - 3h; Heating / reflux;

(3-methoxyphenyl)magnesium bromide; at 0 - 20 ℃; for 1.5h;

With water; ammonium chloride;

Reference yield: 25.0%

4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (186094-10-0) + (-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine (155836-78-5) → (+)-4-[(αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide (156727-74-1) + SNC 79 (156727-75-2)

Guidance literature:

With potassium carbonate; In acetonitrile; for 72h; Heating;

DOI:10.1021/jm960319n

Reference yield:

2,5-dimethyl-piperazine (2815-34-1,1119702-25-8) → (+)-4-[(αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide (156727-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 39.65 g / ethanol / Ambient temperature

3: 29 percent / K₂CO₃ / acetonitrile / 72 h / Heating

With potassium carbonate; In ethanol; acetonitrile;

DOI:10.1021/jm960319n

upstream raw materials:

4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide

(-)-(2R,5S)-1-allyl-2,5-dimethylpiperazine

(3-methoxyphenyl)magnesium bromide

N,N-diethyl-4-formylbenzamide

Downstream raw materials:

4-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

(+)-4-[(αR)-α-((2S,5R)-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide