N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine

Base Information

• Chemical Name: N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine
• CAS No.: 5784-91-8
• Molecular Formula: C₂₃H₂₁NO₂
• Molecular Weight: 343.425
• DSSTox Substance ID: DTXSID50357859
• Mol file: 5784-91-8.mol

Synonyms:STK001461;5784-91-8;CBMicro_033027;Oprea1_802544;DTXSID50357859;N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine;AKOS001630848;BIM-0033152.P001;4-benzyl-N-(4-tert-butylbenzylidene)piperazin-1-amine

Chemical Property of N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine

Chemical Property:

• Vapor Pressure: 6.3E-09mmHg at 25°C
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 335.236147938
• Heavy Atom Count: 25
• Complexity: 404

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C=NN2CCN(CC2)CC3=CC=CC=C3

Technology Process of N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine

There total 13 articles about N-(4-benzylpiperazin-1-yl)-1-(4-tert-butylphenyl)methanimine 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: 98.0%

4,4'-dimethoxydiphenylacetylene (2132-62-9) + 1-methyl-1-phenyl-2-propylidenehydrazine (5311-82-0) → 2,3-bis(4-methoxyphenyl)-1-methyl-1H-indole (5784-91-8)

Guidance literature:

With 1,2,3,4-tetraphenylcyclopentadiene; tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; copper diacetate; In N,N-dimethyl-formamide; at 120 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.016

Reference yield: 94.0%

N-methyl-N-nitrosoaniline (614-00-6) + 4,4'-dimethoxydiphenylacetylene (2132-62-9) → 2,3-bis(4-methoxyphenyl)-1-methyl-1H-indole (5784-91-8)

Guidance literature:

With [Cp*Rh(OAc)2]; In methanol; at 90 ℃; Sealed tube;

DOI:10.1021/ol402523x

Reference yield: 93.0%

1-bromo-4-methoxy-benzene (104-92-7) + N-methyl-1H-indole-2-carboxylic acid (16136-58-6) → 2,3-bis(4-methoxyphenyl)-1-methyl-1H-indole (5784-91-8)

Guidance literature:

With palladium diacetate; caesium carbonate; tricyclohexylphosphine; In o-xylene; for 4h; Inert atmosphere; Reflux;

DOI:10.1002/chem.200900098

upstream raw materials:

indoxole

dimethyl sulfate

1,4-di(4-methoxyphenyl)ethanone

1-Methyl-1-phenylhydrazine

Refernces

• 1、 Li, Bin,Xu, Hong,Wang, Huanan,Wang, Baiquan. "Rhodium-catalyzed annulation of tertiary aniline N-oxides to N-alkylindoles: Regioselective C-H activation, oxygen-atom transfer, and N-dealkylative cyclization". . p. 3856 - 3862. Retrieved 2016/07/06.
• 2、 Matsuda, Takanori,Tomaru, Yuki. "Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2- arylhydrazines and alkynes via C-H and N-N bond cleavages". supporting information. p. 3302 - 3304. Retrieved 2014/06/09.