Benzaldehyde → 2-Methyl-N-(phenylmethylene)-2-propanamine

HRID 1884078Notes

Reaction equation

HRID 1884078 reaction equation
[C:1]1([CH:7]=[N+:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)C1C=CC=CC=1.C(N)(C)(C)C>O>[CH:7](=[N:8][C:10]([CH3:13])([CH3:12])[CH3:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4390N-tert-Butyl-a-phenylnitroneHCID 6385Tert-Butylamine

Product 1

HCID 1112402-Methyl-N-(phenylmethylene)-2-propanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The imine starting material may be commercially purchased or synthetically prepared. If desired, the imine may be prepared by a condensation reaction between an aldehyde and a primary amine. In one embodiment of the present invention, the imine precursor for α-phenyl-N-tert-butyl nitrone (PBN) is prepared by combining benzaldehyde and t-butyl amine at room temperature, in the absence of a solvent, to form the corresponding benzylidene-t-butyl amine (imine) and water. It was found that the resulting imine was sufficiently pure for use in the next step without the need for purification or removal of water by-product contained therein. Thus, the present method reduces time and cost, and improves efficiency, in comparison with traditional transformations.

Workup

  1. customsynthetically prepared
  2. customat room temperature

Sources & evidence

ORD record
ord-011a1c48d53549779cefa04ca71b5e75
Source dataset
uspto-grants-2004_07
Patent number
US06762322B1

Reaction notes

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