Methane → 1,3-bis(N-phenyl-3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

HRID 329698Notes

Reaction equation

HRID 329698 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[CH3:11][SiH:12]([CH3:17])[O:13][SiH:14]([CH3:16])[CH3:15].[CH4:18]>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[C:5]1([NH:4][CH2:1][CH2:2][CH2:3][Si:12]([CH3:17])([CH3:11])[O:13][Si:14]([CH2:18][CH2:2][CH2:1][NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:16])[CH3:15])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 186591,1,3,3-Tetramethyl-disiloxaneHCID 68525N-Allylaniline

Product 1

HCID 198714031,3-bis(N-phenyl-3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

Reagents, catalysts & solvents 1

HCID 61859Chloroplatinic acidCatalyst

Procedure

N-allylaniline (0.200 mole) and 1,1,3,3-tetramethyldisiloxane (0.100 mole) are introduced along with 0.05 g hexachloroplatinic acid into a 100 ml cylindrical glass reactor equipped with reflux condenser, nitrogen inlet, and stir bar. The contents of the reaction are heated and maintained while stirring, at approximately 70° C., for a period of ten hours. The IR spectrum of the resulting viscous oil shows no peaks corresponding to Si-H, indicating completion of the reaction. The crude product is mixed with carbon black and stirred overnight at room temperature. The product is filtered through silica gel and the filter cake washed with toluene. Volatile fractions are removed by stripping under vacuum at 150° C. to give a slightly colored oil. The oil is further purified by vacuum distillation at <1 torr at 223°-230° C. The yield of 1,3-bis(N-phenyl-3-aminopropyl)-1,1,3,3-tetramethyldisiloxane is virtually quantitative.

Workup

  1. customequipped
  2. temperaturewith reflux condenser, nitrogen inlet
  3. temperatureThe contents of the reaction are heated
  4. temperaturemaintained
  5. stirringwhile stirring, at approximately 70° C., for a period of ten hours
  6. customcompletion of the reaction
  7. stirringstirred overnight at room temperature
  8. filtrationThe product is filtered through silica gel
  9. washthe filter cake washed with toluene
  10. customVolatile fractions are removed
  11. customby stripping under vacuum at 150° C.
  12. customto give a slightly colored oil
  13. distillationThe oil is further purified by vacuum distillation at <1 torr at 223°-230° C

Sources & evidence

ORD record
ord-b3c1c43cea734e349539c588f022c8af
Source dataset
uspto-grants-1990_01
Patent number
US04892918

Reaction notes

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