1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone

Base Information

• Chemical Name: 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone
• CAS No.: 1243546-87-3
• Molecular Formula: C₂₅H₃₂N₂O₂
• Molecular Weight: 392.541
• Mol file: 1243546-87-3.mol

Synonyms:1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone

Chemical Property of 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone

There total 7 articles about 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone 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: 50.0%

4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile (1243546-81-7) + methyllithium (917-54-4) → 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone (1243546-87-3)

Guidance literature:

4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile; methyllithium; In tetrahydrofuran; diethyl ether; Cooling with ice;

With water; In tetrahydrofuran; diethyl ether;

Reference yield:

2,3,5-trimethylphenol (697-82-5) → 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone (1243546-87-3)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 80 °C

2: N,N-diethylaniline / 11 h / 220 - 230 °C / Inert atmosphere

3: toluene-4-sulfonic acid / toluene; water / 1.5 h / Reflux

4: N-Bromosuccinimide / acetonitrile / 5 h / 20 °C / Cooling with ice

5: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 16 h / 100 °C / Inert atmosphere

6: hydrogenchloride / ethyl acetate; water / 3 h / 50 °C

7: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 0.25 h / 150 °C / Microwave irradiation

8: tetrahydrofuran; diethyl ether / 3 h / 0 °C

With hydrogenchloride; N-Bromosuccinimide; palladium diacetate; potassium carbonate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-diethylaniline; sodium t-butanolate; In tetrahydrofuran; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2: |Claisen Rearrangement;

DOI:10.1021/acs.jmedchem.6b00191

Reference yield:

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene (142874-36-0) → 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone (1243546-87-3)

Guidance literature:

Multi-step reaction with 7 steps

1: N,N-diethylaniline / 11 h / 220 - 230 °C / Inert atmosphere

2: toluene-4-sulfonic acid / toluene; water / 1.5 h / Reflux

3: N-Bromosuccinimide / acetonitrile / 5 h / 20 °C / Cooling with ice

4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 16 h / 100 °C / Inert atmosphere

5: hydrogenchloride / ethyl acetate; water / 3 h / 50 °C

6: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 0.25 h / 150 °C / Microwave irradiation

7: tetrahydrofuran; diethyl ether / 3 h / 0 °C

With hydrogenchloride; N-Bromosuccinimide; palladium diacetate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-diethylaniline; sodium t-butanolate; In tetrahydrofuran; diethyl ether; water; ethyl acetate; toluene; acetonitrile; 1: |Claisen Rearrangement;

DOI:10.1021/acs.jmedchem.6b00191

upstream raw materials:

4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]benzonitrile

methyllithium

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene

2,3,5-trimethyl-6-(2-methylprop-2-en-1-yl)phenol

Downstream raw materials:

1-{-4-[4-(2,2,4,6,7-Pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanol

Refernces

• 1、 -. "Benzofuran derivatives". Page/Page column 93. . Retrieved 2010/09/18.