Water → 4-benzyl-N,N-diphenylaniline

HRID 446214Notes

Reaction equation

HRID 446214 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([N:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=O)=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:20]([C:17]1[CH:16]=[CH:15][C:14]([N:13]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:19][CH:18]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10545746(4-(Diphenylamino)phenyl)(phenyl)methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 233994894-benzyl-N,N-diphenylanilineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.6 g, 43.0 mmol) was dissolved in purified tetrahydrofuran (30 mL) under a nitrogen atmosphere, and the reaction solution was stirred. A solution prepared by dissolving (4-(diphenylamino)phenyl) (phenyl)methanone (5.0 g, 14.3 mmol) in purified tetrahydrofuran (100 mL) was slowly added thereto at 0° C. The reaction mixture solution was stirred at room temperature for 2 hours, and then distilled water (30 mL) was added to the reaction mixture solution, followed by addition of aqueous sodium hydroxide solution (100 mL). The reaction solution was subjected to extraction with dichloromethane, the solvent was removed from the extracted material, and then the residue material was dried in vacuum to thereby obtain a white solid (4.1 g, yield: 86%).

Workup

  1. customA solution prepared
  2. additionwas slowly added
  3. customat 0° C
  4. stirringThe reaction mixture solution was stirred at room temperature for 2 hours
  5. extractionThe reaction solution was subjected to extraction with dichloromethane
  6. customthe solvent was removed from the extracted material
  7. customthe residue material was dried in vacuum

Sources & evidence

ORD record
ord-173202c4f4714e379ea78816da942b1c
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

Loading…