N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine

Base Information

• Chemical Name: N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine
• CAS No.: 235425-83-9
• Molecular Formula: C₂₉H₃₃N₃O₄S
• Molecular Weight: 519.665

Synonyms:N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine

Chemical Property of N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine

There total 11 articles about N¹-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine 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:

1,3-cylohexanedione (504-02-9) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N4-phenylpiperazine (235425-83-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / Zn, 70 percent AcOH / 45 h / Heating

2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

3: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, a) -70 deg C, 30 min, b) RT, 18 h

4: 75 percent / NaOH / methanol / 2 h / Heating

5: 55 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; zinc; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

Reference yield:

3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (6116-76-3) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N4-phenylpiperazine (235425-83-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

2: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, a) -70 deg C, 30 min, b) RT, 18 h

3: 75 percent / NaOH / methanol / 2 h / Heating

4: 55 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

5: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

Reference yield:

1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (144219-62-5) → N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N4-phenylpiperazine (235425-83-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -70 deg C, 1 h, 2.) THF, a) -70 deg C, 30 min, b) RT, 18 h

2: 75 percent / NaOH / methanol / 2 h / Heating

3: 55 percent / 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

4: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 65 deg C, 12 h

With sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.621

upstream raw materials:

4-phenyl-1-piperazine

ethyl 1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetate

benzenesulfonyl chloride

N¹-(3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N⁴-phenylpiperazine

Downstream raw materials:

N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-phenylpiperazine

N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-phenylpiperazine

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