4-Isopropylaniline → N-(4-(Dimethylamino)benzyl)-4-isopropylbenzenamine

HRID 218542Notes

Reaction equation

HRID 218542 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:19][C:18]2[CH:20]=[CH:21][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74644-IsopropylanilineHCID 74794-(Dimethylamino)Benzaldehyde

Product 1

HCID 21957887N-(4-(Dimethylamino)benzyl)-4-isopropylbenzenamineYield 68.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-dimethylaminobenzaldehyde (11 g) in toluene (200 mL) were added 4-isopropylaniline (10 g) and molecular sieves 4A (20 g) under ice-cooling, and the mixture was stirred at room temperature for one day. The molecular sieves 4A was filtered off from the reaction mixture, and the obtained filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (200 mL) and sodium borohydride (2.3 g) was added under ice-cooling. The mixture was stirred at room temperature for 5 hr. After methanol was distilled away, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give (4-dimethylaminophenylmethyl)(4-isopropylphenyl)amine (13.6 g). melting point: 71-73° C.

Workup

  1. temperaturecooling
  2. filtrationThe molecular sieves 4A was filtered off from the reaction mixture
  3. concentrationthe obtained filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (200 mL)
  5. additionsodium borohydride (2.3 g) was added under ice-
  6. temperaturecooling
  7. stirringThe mixture was stirred at room temperature for 5 hr
  8. distillationAfter methanol was distilled away
  9. additionwater was added to the residue
  10. extractionthe mixture was extracted with chloroform
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-00378eedb07149d8a9200f5f65603f7a
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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