4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester
• CAS No.: 133407-24-6
• Molecular Formula: C₁₉H₂₃Cl₂N₃O₄
• Molecular Weight: 428.315
• Mol file: 133407-24-6.mol

Synonyms:4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester

Chemical Property of 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester

There total 8 articles about 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester 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:

3,4-dichlorophenyl acetic acid (5807-30-7) → 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester (133407-24-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) 1,1'-carbonyldiimidazole / 1.) dichloromethane, RT, 1 h, 2.) dichloromethane, RT, 18 h

2: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

3: 55 percent / 3A molecular sieves, HCl, NaBH₃CN / methanol / 18 h

4: 88 percent / H₂, aq. HCl / 10percent Pd/C / tetrahydrofuran / 0.25 h / 760 Torr

5: 76 percent / Et₃N / CH₂Cl₂ / 0.5 h / -25 °C

6: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

With hydrogenchloride; oxalyl dichloride; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00067a004

Reference yield:

ethyl 3-oxo-4-(phenylmethyl)-2-piperazinecarboxylate (149648-71-5) → 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester (133407-24-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 67 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

2: 1.) 1,1'-carbonyldiimidazole / 1.) dichloromethane, RT, 1 h, 2.) dichloromethane, RT, 18 h

3: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

4: 55 percent / 3A molecular sieves, HCl, NaBH₃CN / methanol / 18 h

5: 88 percent / H₂, aq. HCl / 10percent Pd/C / tetrahydrofuran / 0.25 h / 760 Torr

6: 76 percent / Et₃N / CH₂Cl₂ / 0.5 h / -25 °C

7: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

With hydrogenchloride; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00067a004

Reference yield:

1-<(3,4-dichlorophenyl)acetyl>-4-(phenylmethyl)-2-piperazinemethanol (126766-44-7) → 4-[2-(3,4-Dichloro-phenyl)-acetyl]-3-(3-oxo-pyrrolidin-1-ylmethyl)-piperazine-1-carboxylic acid methyl ester (133407-24-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

2: 55 percent / 3A molecular sieves, HCl, NaBH₃CN / methanol / 18 h

3: 88 percent / H₂, aq. HCl / 10percent Pd/C / tetrahydrofuran / 0.25 h / 760 Torr

4: 76 percent / Et₃N / CH₂Cl₂ / 0.5 h / -25 °C

5: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) dichloromethane, -60 deg C, 2.5 h, 2.) dichloromethane, from -60 deg C to -20 deg C

With hydrogenchloride; oxalyl dichloride; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00067a004

upstream raw materials:

methyl 4-[(3,4-dichlorophenyl)acetyl]-3-[(3-hydroxy-1-pyrrolidinyl)-methyl]-1-piperazinecarboxylate

3,4-dichlorophenyl acetic acid

ethyl 3-oxo-4-(phenylmethyl)-2-piperazinecarboxylate

1-<(3,4-dichlorophenyl)acetyl>-4-(phenylmethyl)-2-piperazinemethanol

Refernces