4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

Base Information

• Chemical Name: 4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide
• CAS No.: 156727-71-8
• Molecular Formula: C₂₈H₃₉N₃O₂
• Molecular Weight: 449.637
• DSSTox Substance ID: DTXSID90861420
• Nikkaji Number: J761.721F
• ChEMBL ID: CHEMBL611159
• Mol file: 156727-71-8.mol

Synonyms:CHEMBL611159;SNC-79;DTXSID90861420;156727-71-8;4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

Chemical Property of 4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

Chemical Property:

• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

Technology Process of 4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

There total 15 articles about 4-[(S)-[(2R,5S)-2,5-Dimethyl-4-(2-propen-1-yl)-1-piperazinyl](3-methoxyphenyl)methyl]-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: 29.0%

4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (186094-10-0) + (+)-(2S,5R)-1-allyl-2,5-dimethylpiperazine (155836-79-6) → SNC 83 (156727-72-9) + SNC 67 (156727-71-8)

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) → SNC 67 (156727-71-8)

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

Reference yield:

(4-methylphenyl)-(3-methoxyphenyl)methanone (82520-37-4) → SNC 67 (156727-71-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 53 percent / KMnO₄ / 2-methyl-propan-2-ol; H₂O / 7.5 h / Heating

2: SOCl₂ / benzene / 3 h / Heating

3: CHCl₃ / 4 h / Ambient temperature

4: 70 percent / NaBH₄ / ethanol; H₂O / 2 h / Heating

5: 11.16 g / 37percent aq. HCl / CHCl₃ / Ambient temperature

6: 29 percent / K₂CO₃ / acetonitrile / 72 h / Heating

With hydrogenchloride; sodium tetrahydroborate; potassium permanganate; thionyl chloride; potassium carbonate; In ethanol; chloroform; water; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/jm960319n

upstream raw materials:

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

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

(3-methoxyphenyl)magnesium bromide

N,N-diethyl-4-formylbenzamide

Downstream raw materials:

SNC 89

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

Refernces

• 1、 Calderon, Silvia N.,Rice, Kenner C.,Rothman, Richard B.,Porreca, Frank,Flippen-Anderson, Judith L.,Kayakiri, Hiroshi,Xu, Heng,Becketts, Karen,Smith, Larren E.,Bilsky, Edward J.,Davis, Peg,Horvath, Robert. "Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]N,N- diethylbenzamide (SNC 80) and related novel nonpeptide δ opioid receptor ligands". . p. 695 - 704. Retrieved 2007/10/03.