(1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione

Base Information

• Chemical Name: (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione
• CAS No.: 138332-82-8
• Molecular Formula: C₂₃H₃₀ClN₃O₂
• Molecular Weight: 415.963

Synonyms:(1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione

Chemical Property of (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione

Chemical Property:

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Technology Process of (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione

There total 4 articles about (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.0^2,6]decane-3,5-dione 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: 55.7%

(1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide (99095-09-7) + N-(m-chlorophenyl)piperazine (6640-24-0) → (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione (138332-82-8)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1248/cpb.39.2288

Reference yield:

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2) → (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione (138332-82-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95.9 percent / H₂ / 10percent Pd-C/ 50percent H₂O / tetrahydrofuran / 1.5 h / Ambient temperature

2: 80.5 percent / 7percent aq. NH₃ / tetrahydrofuran / 2 h / 190 °C

3: 90.2 percent / K₂CO₃ / acetone / 7 h / Heating

4: 55.7 percent / K₂CO₃, KI / dimethylformamide / 90 °C

With ammonium hydroxide; hydrogen; potassium carbonate; potassium iodide; palladium on activated charcoal; water; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.39.2288

Reference yield:

(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione (14805-29-9,1318027-24-5) → (1S,2R,6S,7R)-4-{4-[4-(3-Chloro-phenyl)-piperazin-1-yl]-butyl}-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione (138332-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.2 percent / K₂CO₃ / acetone / 7 h / Heating

2: 55.7 percent / K₂CO₃, KI / dimethylformamide / 90 °C

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.39.2288

upstream raw materials:

(1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide

N-(m-chlorophenyl)piperazine

(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

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