1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]

Base Information

• Chemical Name: 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]
• CAS No.: 917898-66-9
• Molecular Formula: C₂₄H₃₁N₃O₂
• Molecular Weight: 393.529

Synonyms:1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]

Chemical Property of 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]

There total 8 articles about 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline] 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: 90.0%

1-neopentyl-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline] (917898-65-8) + 2-nitrophenyl bromide (577-19-5) → 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline] (917898-66-9)

Guidance literature:

With caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100 ℃;

Reference yield:

pivaloyl chloride (3282-30-2) → 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline] (917898-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 4 h / 23 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 23 °C / Inert atmosphere

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene / 16 h / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 3: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm4013906

Reference yield:

Spiro(2-oxo-1,2,3,4-tetrahydroquinoline-4,4'-piperidine) (159634-63-6) → 1-neopentyl-1'-(2-nitrophenyl)-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline] (917898-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 4 h / 23 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 23 °C / Inert atmosphere

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene / 16 h / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 3: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm4013906

upstream raw materials:

1-neopentyl-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]

2-nitrophenyl bromide

pivaloyl chloride

spiro[1H-indene-1,4'-piperidin]-3(2H)-one

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