4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide

Base Information

• Chemical Name: 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide
• CAS No.: 1338603-77-2
• Molecular Formula: C₂₈H₂₉ClN₂O
• Molecular Weight: 445.004
• Mol file: 1338603-77-2.mol

Synonyms:4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide

Chemical Property of 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide

There total 6 articles about 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-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: 8.0%

4'-chloro-N-[6-(chloro-methyl)-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide + diethylamine (109-89-7) → 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide (1338603-77-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 120 ℃; for 48h;

DOI:10.1016/j.bmc.2011.07.038

Reference yield:

6-amino-2-[(dimethylamino)methylidene]-3,4-dihydro-1(2H)-naphthalenone → 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide (1338603-77-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 0.5 h / Cooling with ice

1.2: 1 h / Cooling with ice

2.1: hydrogenchloride; water / 6 h / 100 °C

3.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 4 h

4.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 20 h / 20 °C / Cooling with ice

5.1: CHIRALCEL OD column / ethanol; hexane / Resolution of racemate

6.1: chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / -78 - 20 °C

7.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 120 °C

With hydrogenchloride; dmap; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.07.038

Reference yield:

C13H20N2O → 4'-chloro-N-[6-[(N,N-diethylamino)methyl]-7,8-dihydro-2-naphthalenyl][1,1'-biphenyl]-4-carboxamide (1338603-77-2)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride; water / 6 h / 100 °C

2: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 4 h

3: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 20 h / 20 °C / Cooling with ice

4: CHIRALCEL OD column / ethanol; hexane / Resolution of racemate

5: chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / -78 - 20 °C

6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 120 °C

With hydrogenchloride; dmap; palladium 10% on activated carbon; water; hydrogen; chloroformic acid ethyl ester; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.07.038

upstream raw materials:

[(6-amino-1,2,3,4-tetrahydro-2-naphthalenyl)methyl]dimethylamine

diethylamine