Benzaldehyde → Ethenamine, 2-phenyl-

HRID 247746Notes

Reaction equation

HRID 247746 reaction equation
[CH3:1][NH2:2].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1(C)C=CC=CC=1>[CH:3](=[CH:1][NH2:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 6329Methylamine3×

Product 1

HCID 155076Ethenamine, 2-phenyl-Yield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous monomethylamine (about 1-1.5 eq.) was introduced below the surface of a stirred solution of benzaldehyde (1062 g, 10.0 mol) in toluene (2000 ml) cooled to 0° C. The rate of addition of monomethylamine was adjusted so as to maintain the reaction temperature between 25°-30° C.; after 45 minutes the addition of monomethylamine was terminated. The organic phase was separated and concentrated in vacuo. Distillation of the residual oil afforded N-benzylidenemethylamine (1047 g, 8.79 mol) in 88% yield. The product had a boiling point of 79° C. at 20 mm. [This N-benzylidinemethylamine starting material is reported by R. B. Moffett et al, Org. Syn. Coll. Vol. IV, 605-608 (1963)].

Workup

  1. temperatureto maintain the reaction temperature between 25°-30° C.
  2. customwas terminated
  3. customThe organic phase was separated
  4. concentrationconcentrated in vacuo
  5. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-d83d13a1e5c64056b2660fff20a6be7a
Source dataset
uspto-grants-1987_11
Patent number
US04709093

Reaction notes

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