Allylamine → Allylamine

HRID 330597Notes

Reaction equation

HRID 330597 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(O[SiH](OCC)OCC)C.N[CH2:16][CH2:17][CH2:18][Si:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>[Rh].CC1C=CC(C)=CC=1>[CH2:1]([NH2:4])[CH:2]=[CH2:3].[NH2:4][CH:17]([CH3:16])[CH2:18][Si:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]

Participants

7

Reactant 3

HCID 7853AllylamineHCID 13521(3-Aminopropyl)triethoxysilaneHCID 13830Triethoxysilane2×

Product 2

HCID 7853AllylamineHCID 10236113HCID 10236113, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

A three-neck flask equipped with a reflux condenser, stirring rod and thermometer was charged with 14 grams of allylamine (0.25 mole), 41 grams of triethoxy silane (0.25 mole), 20 ml. of p-xylene and 0.1% by mole (calculated as rhodium), per mole of triethoxysilane, of [Rh(μ-P Ph2) (COD)]2, that is [rhodium(μ-diphenyl phosphide) (1,5-cyclooctadiene) dimer], and heated on an oil bath maintained at a temperature of 110° C. About 1 hour after the beginning of the reaction, the reaction temperature reached 110° C. At the end of the period the reaction mixture was subjected to gas chromatography analysis. It was found that gamma-aminopropyl triethoxy silane was obtained in a yield of 81% on an allylamine basis, while the yield of beta-aminopropyl triethoxy silane was 0.7% on a triethoxy silane basis.

Workup

  1. customA three-neck flask equipped with a reflux condenser
  2. temperatureheated on an oil bath
  3. customAbout 1 hour after the beginning of the reaction
  4. customreached 110° C

Sources & evidence

ORD record
ord-e97171a3f19846d1bd33566ebb6b07ca
Source dataset
uspto-grants-1990_01
Patent number
US04897501

Reaction notes

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