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

Base Information

• Chemical Name: N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine
• CAS No.: 165963-43-9
• Molecular Formula: C₃₀H₃₉N₃O₄S
• Molecular Weight: 537.723

Synonyms:N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine

Chemical Property of N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine

Chemical Property:

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Technology Process of N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine

There total 13 articles about N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N⁴-(o-methoxyphenyl)piperazine 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: 82.0%

N1-(1-benzenesulfonyl-3-ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydro-5-indolylacetyl)-N4-(o-methoxyphenyl)piperazine (165963-42-8) → N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N4-(o-methoxyphenyl)piperazine (165963-43-9)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1248/cpb.47.621

Reference yield:

1,3-cylohexanedione (504-02-9) → N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N4-(o-methoxyphenyl)piperazine (165963-43-9)

Guidance literature:

Multi-step reaction with 7 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: 1.) 1-hydroxybenzotriazole, 2.) dicyclohexylcarbodiimide / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 h

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

7: 82 percent / AlH₃ / tetrahydrofuran / 12 h / Ambient temperature

With aluminium hydride; sodium hydroxide; sodium hydride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1248/cpb.47.621

Reference yield:

3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (6116-76-3) → N-<β-(1-benzenesulfonyl-3-ethyl-2-methyl-4-hydroxy-4,5,6,7-tetrahydro-5-indolyl)ethyl>-N4-(o-methoxyphenyl)piperazine (165963-43-9)

Guidance literature:

Multi-step reaction with 6 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: 1.) 1-hydroxybenzotriazole, 2.) dicyclohexylcarbodiimide / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 h

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

6: 82 percent / AlH₃ / tetrahydrofuran / 12 h / Ambient temperature

With aluminium hydride; sodium hydroxide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1248/cpb.47.621

upstream raw materials:

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

1-(2-Methoxyphenyl)piperazine

1,3-cylohexanedione

3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole

Downstream raw materials:

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

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