3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide

Base Information

• Chemical Name: 3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide
• CAS No.: 119878-31-8
• Molecular Formula: C₁₈H₂₄Br₂N₂O
• Molecular Weight: 444.209
• ChEMBL ID: CHEMBL279065
• DSSTox Substance ID: DTXSID901031667
• Mol file: 119878-31-8.mol

Synonyms:CHEMBL279065;DTXSID901031667;BDBM50017059;3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide

Chemical Property of 3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 444.02349
• Heavy Atom Count: 23
• Complexity: 447

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCCC12CCCCC2N(C)C(=O)C3=CC(=C(C=C3)Br)Br
• Isomeric SMILES: CN1CCC[C@@]12CCCC[C@@H]2N(C)C(=O)C3=CC(=C(C=C3)Br)Br
• Description: U-77891 is an opioid analgesic drug that was first synthesized in 1983 by the Upjohn company.[1] It was originally synthesized to prove that the removal of a single methylene spacer of the benzamide would alter a κ-opioid receptor agonist such as U-50488 into an μ-opioid receptor agonist, as well as producing a semi-rigid derivative of U-47700. This would help elucidate the relative positions of the hydrogen-bond acceptors and substituted aromatic system to find the compound with the lowest Ki value in a series of benzamide opioids dating back to the 1970s.[2] The original work found a mixture of agonists and antagonists. wikipedia
• Uses: trans-3,4-Dibromo-N-methyl-N-(1-methyl-1-azaspiro[4.5]dec-6-yl)-benzamide is a μ-opioid, δ-opioid and κ-opioid receptors agonist and an analgesic agent.

Technology Process of 3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide

There total 10 articles about 3,4-Dibromo-N-methyl-N-(1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide 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: 81.0%

3,4-dibromobenzoyl chloride (21900-35-6) + N,1-dimethyl-1-azaspiro<4.5>decan-10-amine (119878-17-0) → 3,4-Dibromo-N-methyl-N-((5S,6R)-1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide (119878-31-8)

Guidance literature:

With triethylamine; In dichloromethane; for 1h;

DOI:10.1021/jm00126a019

Reference yield:

3-(cyclohexa-1,4-dien-1-yl)propan-1-amine (21797-84-2) → 3,4-Dibromo-N-methyl-N-((5S,6R)-1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide (119878-31-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 62 g / pyridine / 18 h / Ambient temperature

2: 76 percent / H₂ / tris(triphenylphosphine)rhodium(I) chloride / tetrahydrofuran / 24 h / 760 Torr

3: 60 percent / m-chloroperbenzoic aicd / CH₂Cl₂ / 18 h / Ambient temperature

4: 70 percent / BF₃*Et₂O / CH₂Cl₂ / a) -78 deg C, 3.5 h, b) -78 deg C to r.t.

5: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 18 h

6: 89 percent / pyridine / 18 h

7: 1.3 g / LAH / tetrahydrofuran / 5 h / Ambient temperature

8: 97 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

9: 78 percent / LAH / tetrahydrofuran / 1.5 h / Ambient temperature

10: 81 percent / Et₃N / CH₂Cl₂ / 1 h

With pyridine; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00126a019

Reference yield:

benzyl N-<3-(1,4-cyclohexadien-1-yl)propyl>carbamate (119878-56-7) → 3,4-Dibromo-N-methyl-N-((5S,6R)-1-methyl-1-aza-spiro[4.5]dec-6-yl)-benzamide (119878-31-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / H₂ / tris(triphenylphosphine)rhodium(I) chloride / tetrahydrofuran / 24 h / 760 Torr

2: 60 percent / m-chloroperbenzoic aicd / CH₂Cl₂ / 18 h / Ambient temperature

3: 70 percent / BF₃*Et₂O / CH₂Cl₂ / a) -78 deg C, 3.5 h, b) -78 deg C to r.t.

4: 100 percent / pyridinium chlorochromate / CH₂Cl₂ / 18 h

5: 89 percent / pyridine / 18 h

6: 1.3 g / LAH / tetrahydrofuran / 5 h / Ambient temperature

7: 97 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

8: 78 percent / LAH / tetrahydrofuran / 1.5 h / Ambient temperature

9: 81 percent / Et₃N / CH₂Cl₂ / 1 h

With pyridine; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00126a019

upstream raw materials:

3,4-dibromobenzoyl chloride

N,1-dimethyl-1-azaspiro<4.5>decan-10-amine

3-(cyclohexa-1,4-dien-1-yl)propan-1-amine

ethyl N-(1-methyl-1-azaspiro<4.5>decan-10-yl)carbamate