Benzaldehyde → 2,2-Dimethoxy-N-(phenylmethylene)-1-ethanamine

HRID 2399930Notes

Reaction equation

HRID 2399930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][NH2:13]>O>[CH:1](=[N:13][CH2:12][CH:11]([O:14][CH3:15])[O:10][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 127874042,2-Dimethoxy-N-(phenylmethylene)-1-ethanamineYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a three neck round bottom flask, equipped with a cold water condenser, 20 g of water and 21.2 g of benzaldehyde were added. The reactants were mixed using a magnetic stirrer at room temperature for 3 minutes. Aminoacetaldehyde dimethyl acetal (21 g) was added to the reaction flask in one portion, followed by vigorous stirring for 2.5 hours. The agitation was stopped and the reaction mixture was allowed to stand for at least 15 minutes. The lower aqueous layer was separated and discard. The upper layer was collected and washed with saturated sodium chloride solution. The organic layer was collected and dried over magnesium sulfate to give 20.4 g of product. 1H NMR (300 Hz, CDCl3, ppm): 8.26 (1H, s), 7.65 (2H, m), 7.40 (3H, m), 4.66 (1H, t, J=5.3 Hz), 3.77 (2H, d,d, J=5.3 Hz, J=1.5 Hz), 3.39 (6H, s).

Workup

  1. customTo a three neck round bottom flask, equipped with a cold water condenser
  2. additionThe reactants were mixed
  3. customat room temperature
  4. customfor 3 minutes
  5. waitto stand for at least 15 minutes
  6. customThe lower aqueous layer was separated
  7. customThe upper layer was collected
  8. washwashed with saturated sodium chloride solution
  9. customThe organic layer was collected
  10. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-a06b84d275a149fe848cd35448523b7e
Source dataset
uspto-grants-1995_09
Patent number
US05451653

Reaction notes

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