Benzaldehyde → 2-Propanamine, N-(phenylmethylene)-

HRID 2399927Notes

Reaction equation

HRID 2399927 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([NH2:12])([CH3:11])[CH3:10]>O>[CH:1](=[N:12][CH:9]([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 6363Isopropylamine

Product 1

HCID 959622-Propanamine, N-(phenylmethylene)-Yield 105.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a three neck round bottom flask, equipped with a cold water condenser, 30 g of water and 26.5 g of benzaldehyde were added. The mixture was mixed using a magnetic stirrer for 3 minutes at room temperature. i-Propylamine (17.7 g) was added to the reaction flask in one portion, followed by vigorous stirring for 40 minutes. The agitation was stopped and the reaction mixture was allowed to stand for at least 15 minutes. The lower aqueous layer was separated from the reaction mixture. The upper layer was collected and dried over magnesium sulfate to give 38.9 g of product. This crude product could be further purified by distillation, collecting the fraction between 94°-95° C./18 mmHg. 1H NMR (300 Hz, CDCl3, ppm): 8.29 (1H, s), 7.70 (2H, m), 7.38 (3H, m), 3.53 (hep. J=6.3 Hz), 1.27 (9H, d, J=6.3 Hz); IR (NaCl film, cm-1): 3061, 3026, 2930, 2835, 1647, 1581, 1450, 1382, 1306, 1141,967, 755, 693.

Workup

  1. customTo a three neck round bottom flask, equipped with a cold water condenser
  2. additionThe mixture was mixed
  3. customfor 3 minutes
  4. customat room temperature
  5. waitto stand for at least 15 minutes
  6. customThe lower aqueous layer was separated from the reaction mixture
  7. customThe upper layer was collected
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-afe7615cc45d4849b7821a2f433dd492
Source dataset
uspto-grants-1995_09
Patent number
US05451653

Reaction notes

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