Phenyl-1-naphthylamine → N-(4-Bromophenyl)-N-phenyl-1-naphthylamine

HRID 751745Notes

Reaction equation

HRID 751745 reaction equation
CNCCNC.[C:7]1([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1.C(O[Na])(C)(C)C>[Cu].C1(C)C(C)=CC=CC=1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([N:13]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 7013Phenyl-1-naphthylamineHCID 8070N,N'-DimethylethylenediamineHCID 115221-Bromo-4-iodobenzeneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 18398525N-(4-Bromophenyl)-N-phenyl-1-naphthylamineYield 68.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Procedure

Adding 17.6 g of N,N′-dimethylethylenediamine into a solution prepared by mixing 21.9 g of N-phenyl-1-naphthylamine, 28.2 g of 4-bromoiodobenzene, 14.4 g of t-butoxysodium, 3.81 g of copper powder and 100 milliliter of xylene, the resultant solution was refluxed with heating under ambient atmosphere of argon gas for 24 hours. After cooling the resultant solution down to a room temperature, the solution was filtered and insolubles were removed followed by concentrating the filtrate. Refining the residue by means of a silicagel column chromatography, 25.4 g of N-(4-bromophenyl)-N-phenyl-1-naphthylamine was obtained.

Workup

  1. customprepared
  2. temperaturewith heating under ambient atmosphere of argon gas for 24 hours
  3. filtrationthe solution was filtered
  4. custominsolubles were removed
  5. concentrationby concentrating the filtrate

Sources & evidence

ORD record
ord-e958a2bf58af427cb31fe487c6a93475
Source dataset
uspto-grants-2008_07
Patent number
US07405326B2

Reaction notes

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