Triethylamine → N,N,N-Triethyl-3-(trimethoxysilyl)propan-1-aminium chloride

HRID 537715Notes

Reaction equation

HRID 537715 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][O:9][Si:10]([CH2:15][CH2:16][CH2:17][Cl:18])([O:13][CH3:14])[O:11][CH3:12]>C(OCC)(=O)C>[Cl-:18].[CH3:8][O:9][Si:10]([CH2:15][CH2:16][CH2:17][N+:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2])([O:13][CH3:14])[O:11][CH3:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 624493-(Trimethoxysilyl)propyl chloride

Product 1

HCID 14552288N,N,N-Triethyl-3-(trimethoxysilyl)propan-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3.0 g of triethylamine and 18 g of ethyl acetate 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 8.8 g of trimethoxysilylpropyl chloride was dissolved in 24 g of ethyl acetate was gradually added at room temperature in a nitrogen atmosphere. The reaction mixture was refluxed over 3 days and therefrom, ethyl acetate was distilled off under reduced pressure. The resultant concentrate was dropped into 100 mL of diethyl ether and therefrom, triethylamine and trimethoxysilylpropyl chloride 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 trimethoxysilylpropyltriethylammonium chloride.

Workup

  1. dissolutionto be dissolved
  2. additionmixed solution with a magnetic stirrer
  3. additionwas gradually added at room temperature in a nitrogen atmosphere
  4. temperatureThe reaction mixture was refluxed over 3 days
  5. distillationethyl acetate was distilled off under reduced pressure
  6. concentrationThe resultant concentrate
  7. additionwas dropped into 100 mL of diethyl ether
  8. customtriethylamine and trimethoxysilylpropyl chloride 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-974680eea82c49058ee7950689bd7a2a
Source dataset
uspto-grants-2014_10
Patent number
US08864894B2

Reaction notes

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