1-Propanamine, N,N-dimethyl-3-(trimethoxysilyl)- → Trimethoxysilylpropyldimethylammonium maleate

HRID 537713Notes

Reaction equation

HRID 537713 reaction equation
[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])([O:6][CH3:7])[O:4][CH3:5].[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]\[C:17]([OH:19])=[O:18]>CO>[C:14]([O-:21])(=[O:20])/[CH:15]=[CH:16]\[C:17]([O-:19])=[O:18].[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][NH+:11]([CH3:13])[CH3:12])([O:4][CH3:5])[O:6][CH3:7].[CH3:1][O:2][Si:3]([CH2:8][CH2:9][CH2:10][NH+:11]([CH3:13])[CH3:12])([O:4][CH3:5])[O:6][CH3:7]

Participants

4

Reactant 2

HCID 756681-Propanamine, N,N-dimethyl-3-(trimethoxysilyl)-HCID 444266Maleic Acid

Product 1

HCID 86654370Trimethoxysilylpropyldimethylammonium maleate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5.0 g of trimethoxysilylpropyldimethylamine and 18 g of methanol were charged into a 100 mL flask to be dissolved. While stirring the resultant mixed solution with a magnetic stirrer, to the mixed solution, a solution in which 4.2 g of maleic acid was dissolved in 24 g of methanol was gradually added at room temperature in a nitrogen atmosphere. The reaction mixture was stirred for half a day and therefrom, methanol was distilled off under reduced pressure. The resultant concentrate was dropped into 100 mL of diethyl ether and therefrom, trimethoxysilylpropyldimethylamine and maleic acid as by-products were removed. This purification was repeated three times and then remaining diethyl ether was distilled off under reduced pressure, followed by dissolving the resultant concentrate in methanol to obtain a 30% methanol solution of trimethoxysilylpropyldimethylammonium maleate.

Workup

  1. dissolutionto be dissolved
  2. additionmixed solution with a magnetic stirrer
  3. additionwas gradually added at room temperature in a nitrogen atmosphere
  4. stirringThe reaction mixture was stirred for half a day
  5. distillationmethanol was distilled off under reduced pressure
  6. concentrationThe resultant concentrate
  7. additionwas dropped into 100 mL of diethyl ether
  8. customtrimethoxysilylpropyldimethylamine and maleic acid as by-products were removed
  9. customThis purification
  10. distillationremaining diethyl ether was distilled off under reduced pressure
  11. dissolutionby dissolving the resultant
  12. concentrationconcentrate in methanol

Sources & evidence

ORD record
ord-19cfdc5d95c44fadbcbeee62fd9d3abf
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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