The Synthetic Routes of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE

The synthesis of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE is a complex organic synthesis that involves a number of steps and intermediate products.
The following is a general overview of the synthetic routes for this compound.

Step 1: Naphthalene-1,4-diamine
The synthesis of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE begins with the synthesis of naphthalene-1,4-diamine, which is a primary intermediate.
Naphthalene-1,4-diamine can be synthesized through several routes, including the following:

• Hydrogenation of naphthalene (1) in the presence of a suitable catalyst, such as Pd/C or Ni/Al2O3, and subsequent reduction with sodium borohydride or lithium aluminum hydride.
  
• Resolution of 2-chloro-1,4-benzoxazepine (2) with 1,4-naphthoquinone (3) in the presence of a suitable resolving agent, such as N-phenylphthalimide or N-acetylphenylhydrazine, followed by reduction with lithium aluminum hydride.
  
• Nitration of naphthalene (1) with nitric acid and subsequent reduction with sodium borohydride or lithium aluminum hydride.
  

Step 2: N-(1-Naphthyl)-N-phenyl-aminotriphenylamine
The next step in the synthesis of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE is the synthesis of N-(1-Naphthyl)-N-phenyl-aminotriphenylamine (4), which is a secondary intermediate.
This compound can be synthesized through the following steps:

• Pyridine mediated condensation of 2-chloro-1,4-benzoxazepine (2) and triphenylamine (5) in the presence of a suitable base, such as sodium carbonate or potassium carbonate.
  
• Nitration of N-(1-Naphthyl)-N-phenyl-aminotriphenylamine (4) with nitric acid to introduce the naphthalene-1,4-diamine moiety.
  

Step 3: 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE
The final step in the synthesis of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE is the condensation of N-(1-Naphthyl)-N-phenyl-aminotriphenylamine (4) with 4,4',4''-triphenylamine (6) in the presence of a suitable coupling agent, such as dicyclohexylcarbodiimide (DCC) or hydroxyquinone.
This reaction typically proceeds under pre-cooled conditions, in the presence of anhydrous DMF or anhydrous sulfuric acid, to prevent breakdown of the coupling agent.

Overall, the synthesis of 4,4',4''-TRIS(N-(1-NAPHTHYL)-N-PHENYL-AMINO)-TRIPHENYLAMINE involves several intermediate steps,