ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate

Base Information

• Chemical Name: ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate
• CAS No.: 122858-13-3
• Molecular Formula: C₁₈H₂₁F₂NO₄
• Molecular Weight: 353.366
• Mol file: 122858-13-3.mol

Synonyms:ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate

Chemical Property of ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate

There total 10 articles about ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate 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:

magnesium bis(3-ethoxy-3-oxopropanoate) (37517-78-5) + 4-(1-acetyl-4-piperidinyl)-2,5-difluorobenzoic acid (122858-14-4) → ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate (122858-13-3)

Guidance literature:

With hydrogenchloride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; ethyl acetate;

Reference yield:

1,4-dibromo-2,5-difluorobenzene (327-51-5) → ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate (122858-13-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-butyllithium / 1.) ethyl ether, hexane, -75 deg C, 2.) ethyl ether, hexane, -50 deg C, 30 min

2: 80 percent / p-toluenesulfonic acid / toluene / 16 h / Heating

3: 63.5 percent / dimethylformamide / 20 h / Heating

4: 9.95 g / 6N HCl / 23 h / Heating

5: 77 percent / 0.75 h / Heating

6: 97 percent / H₂ / 10percent Pd/C / acetic acid / 0.1 h / 30 °C / 2585.7 Torr

7: tetrahydrofuran / 1.5 h / Ambient temperature

8: tetrahydrofuran / 1. RT, overnight, 2.) reflux, 1.5 h

With hydrogenchloride; n-butyllithium; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00066a005

Reference yield:

4-(4-bromo-2,5-difluorophenyl)-1-(ethoxycarbonyl)-1,2,3,6-tetrahydropyridine (122858-42-8) → ethyl 4-(1-acetyl-4-piperidinyl)-2,5-difluoro-β-oxobenzenepropionate (122858-13-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 63.5 percent / dimethylformamide / 20 h / Heating

2: 9.95 g / 6N HCl / 23 h / Heating

3: 77 percent / 0.75 h / Heating

4: 97 percent / H₂ / 10percent Pd/C / acetic acid / 0.1 h / 30 °C / 2585.7 Torr

5: tetrahydrofuran / 1.5 h / Ambient temperature

6: tetrahydrofuran / 1. RT, overnight, 2.) reflux, 1.5 h

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00066a005

upstream raw materials:

magnesium bis(3-ethoxy-3-oxopropanoate)

1,4-dibromo-2,5-difluorobenzene

4-(4-bromo-2,5-difluorophenyl)-1-(ethoxycarbonyl)-1,2,3,6-tetrahydropyridine

4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridinyl)-2,5-difluorobenzoic acid