Aniline → N-phenyltriphenylen-2-amine

HRID 2091441Notes

Reaction equation

HRID 2091441 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:32]=[CH:31][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=1.CC(C)([O-])C.[Na+].[NH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:40]1([NH:39][C:15]2[CH:32]=[CH:31][C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[CH:16]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

8

Reactant 4

HCID 6115AnilineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 183811742-BromotriphenyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 58362099N-phenyltriphenylen-2-amineYield 38.5%

Reagents, catalysts & solvents 3

HCID 1140TolueneCatalystHCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Palladium acetate (0.01 g, 0.06 mmol) and 1.0 M tri(t-butyl)phosphine solution in toluene (0.02 mL, 0.02 mmol) were added to a three-neck flask under nitrogen. 100 mL of toluene was then added. The solution was stirred under nitrogen until the color disappeared. To the solution was added 2-bromotriphenylene (2 g, 6.5 mmol), sodium tert-butoxide (0.94 g, 9.8 mmol), and aniline (1.8 g, 20 mmol) in sequence. The mixture was then heated up to reflux overnight. After cooled to room temperature, the mixture was filtered through a celite bed and washed thoroughly with dichloromethane. The product was purified by column chromatography using 1:7 dichloromethane and hexanes as eluent. 0.8 g of desired product was obtained after purification.

Workup

  1. temperatureThe mixture was then heated up
  2. temperatureto reflux overnight
  3. filtrationthe mixture was filtered through a celite bed
  4. washwashed thoroughly with dichloromethane
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-95fb65a4c1ca4f839d00822364b06279
Source dataset
uspto-grants-2013_05
Patent number
US08440326B2

Reaction notes

Loading…