4-(Aminomethyl)benzonitrile → 4-[[(Diphenylmethylene)amino]methyl]benzonitrile

HRID 1282275Notes

Reaction equation

HRID 1282275 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1)#[N:2].[C:11](=N)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:2][CH2:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 826084-(Aminomethyl)benzonitrileHCID 136809Benzophenone imine

Product 1

HCID 184240674-[[(Diphenylmethylene)amino]methyl]benzonitrileYield 164.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

33.73 g (0.2 mol) of 4-cyanobenzylamine and 36.25 g (0.2 mol) of benzophenone imine were dissolved in 540 ml of DCM at room temperature and stirred overnight. The reaction mixture was subsequently washed with 2×90 ml of water and dried with Na2SO4, and the solvent was removed in a rotary evaporator. 55.59 g (93.7%) of the crude product remained. Recrystallization from 550 ml of iPrOH resulted in 97.67 g (80.4%) of pure product. 1H-NMR (CDCl3, δ in ppm): 7.7-7.15 (m, 9H, Ar—H); 4.65 (s, 2H, CH2—N)

Workup

  1. washThe reaction mixture was subsequently washed with 2×90 ml of water
  2. dry with materialdried with Na2SO4
  3. customthe solvent was removed in a rotary evaporator
  4. customRecrystallization from 550 ml of iPrOH

Sources & evidence

ORD record
ord-2f80320c33484b67a4d08d103b8fc0b7
Source dataset
uspto-grants-2002_09
Patent number
US06455671B1

Reaction notes

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