Aniline → N,N,N'-triphenyl-4-phenylenediamine

HRID 2075423

Reaction equation

HRID 2075423 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:4]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

Product 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamineYield 85.1%

Reagents, catalysts & solvents 2

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 1140TolueneSolvent

Procedure

4-bromo triphenylamine 7.6 g (23.45 mmol), aniline 21.85 g (0.235 mol), sodium tert-butoxide 6.76 g (70 mmol), Pd2(dba)3[(tris(dibenzilidene acetone)dipalladium(0))] 0.86 g (0.938 mmol) and tri(tert-butyl)phosphine 0.23 g (1.173 mmol) in 500 ml round bottom flask were dissolved with toluene 200 ml, and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature, and 200 ml of distilled water was added thereto to extract an organic layer. The organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give N,N,N′-triphenyl-p-phenylenediamine (6.71 g, 85%).

Workup

  1. temperaturerefluxed for 12 hours
  2. customAfter the reaction was terminated
  3. addition200 ml of distilled water was added
  4. extractionto extract an organic layer
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. concentrationThe eluate was concentrated
  9. customdried

Sources & evidence

ORD record
ord-f23e98abe15e4424b51dbbadde3f4bdc
Source dataset
uspto-grants-2011_04
Patent number
US07919654B2

Linked notes

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