2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide

Base Information

• Chemical Name: 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide
• CAS No.: 229005-57-6
• Molecular Formula: C₃₆H₄₃N₃O₂
• Molecular Weight: 549.756
• Mol file: 229005-57-6.mol

Synonyms:2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide

Chemical Property of 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide

There total 16 articles about 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide 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: 62.0%

4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (229007-09-4) + 2-(4-piperidinophenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (229007-65-2) → 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (229005-57-6)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20 ℃;

DOI:10.1021/jm9906264

Reference yield:

Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) → 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (229005-57-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N; NaBH(OAc)3 / 1,2-dichloro-ethane / 8 h / 20 °C

2: 100 percent / aq. NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C

3: 79 percent / Fe; AcOH / 20 °C

4: 62 percent / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / 20 °C

With dmap; sodium tris(acetoxy)borohydride; iron; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,2-dichloro-ethane; 1: reductive amination / 2: reductive amination / 3: Reduction / 4: Acylation;

DOI:10.1021/jm9906264

Reference yield:

ethyl glutaroyl chloride (5205-39-0) → 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (229005-57-6)

Guidance literature:

Multi-step reaction with 11 steps

1: AlCl₃ / 3.5 h / 20 °C

2: 2 N aq. NaOH / methanol / 1.5 h / Heating

3: 73 percent / triethylsilane; TFA / 48 h / 55 °C

4: 67 percent / polyphosphoric acid / 12 h / 100 °C

5: 64 percent / NaOMe / 8 h / Heating

6: 86 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -10 °C

7: Et₃N / CH₂Cl₂ / 20 °C

8: 74 percent / DBU / CH₂Cl₂ / 0.5 h / 20 °C

9: 70 percent / tetrakis(triphenylphosphine)palladium; 2 M aq. K₂CO₃ / ethanol; toluene / Heating

10: 100 percent / 1 N aq. NaOH / methanol; tetrahydrofuran / 20 °C

11: 62 percent / 1-hydroxybenzotriazole; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / 20 °C

With triethylsilane; dmap; sodium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; PPA; sodium methylate; potassium carbonate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: Friedel-Crafts reaction / 2: Hydrolysis / 3: Reduction / 4: intramolecular Friedel-Crafts reaction / 5: methoxycarbonylation / 6: Reduction / 7: mesylation / 8: Elimination / 9: Suzuki coupling / 10: Hydrolysis / 11: Acylation;

DOI:10.1021/jm9906264

upstream raw materials:

4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline

2-(4-piperidinophenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

Tetrahydro-4H-pyran-4-one

ethyl glutaroyl chloride