Benzaldehyde → 1-Propanamine, N-(phenylmethylene)-3-(triethoxysilyl)-

HRID 2261504Notes

Reaction equation

HRID 2261504 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH:15](=[N:1][CH2:2][CH2:3][CH2:4][Si:5]([O:12][CH2:13][CH3:14])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 13521(3-Aminopropyl)triethoxysilane

Product 1

HCID 1122621-Propanamine, N-(phenylmethylene)-3-(triethoxysilyl)-Yield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(Imine-TEOS) To a 2000 mL 3-neck round bottom flask placed in an ice water bath and equipped with a stirbar was added 70 g of 5 Å molecular sieves. The flask was then equipped with a reflux condenser and the remaining necks were sealed with rubber septa. The reaction flask was evacuated and backfilled with dry nitrogen three times. After the final backfill cycle, 200.1 g (903.9 mmol) of 3-aminopropyltriethoxysilane was added to the flask, along with 300 mL of anhydrous toluene. With rapid stirring, 95.9 g (903.9 mmol) of benzaldehyde was added dropwise via cannula over 30 minutes. The contents were allowed to stir at room temperature under nitrogen overnight. After an overnight stir, the contents were filtered. An additional 50 mL of anhydrous toluene was added to facilitate the filtration. The filtrate was filtered a second time and collected. The collected filtrate was concentrated via rotary evaporation to yield a pale gold oil (274.9 g, 98%). This solid was isolated in >98% purity, as characterized by 1H NMR spectroscopy and was not purified further. 1H NMR (CDCl3, 400 MHz): 0.68 (m, 2H); 1.22 (m, 9H); 1.85 (m, 2H); 3.61 (m, 2H); 2.82 (m, 6H); 7.40 (m, 3H); 7.72 (m, 2H); 8.27 (s, 1H).

Workup

  1. customequipped with a stirbar
  2. additionwas added 70 g of 5 Å molecular sieves
  3. customThe flask was then equipped with a reflux condenser
  4. customthe remaining necks were sealed with rubber septa
  5. customThe reaction flask was evacuated
  6. stirringAfter an overnight stir
  7. filtrationthe contents were filtered
  8. additionAn additional 50 mL of anhydrous toluene was added
  9. filtrationthe filtration
  10. filtrationThe filtrate was filtered a second time
  11. customcollected
  12. concentrationThe collected filtrate was concentrated via rotary evaporation

Sources & evidence

ORD record
ord-d8a8642d740c4438a2077e41418aece6
Source dataset
uspto-grants-2010_12
Patent number
US07847048B2

Reaction notes

Loading…