Allylamine → Allylamine

HRID 477588Notes

Reaction equation

HRID 477588 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]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Rh].[Rh].[Rh].[Rh].C1(C)C=CC=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 13830Triethoxysilane

Product 2

HCID 7853AllylamineHCID 10236113HCID 10236113, compound

Reagents, catalysts & solvents 2

HCID 994031219584-30-6CatalystHCID 1140TolueneSolvent

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) and 30 ml. of toluene, and heated in an oil bath maintained at a temperature of 110° C. When the temperature of the mixture reached 85° C., 0.22 gram of tetrarhodium dodecacarbonyl was added to the mixture as a catalyst. About 30 minutes after the addition of the catalyst, 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 68% on an allylamine basis, while the yield of beta-aminopropyl triethoxy silane was 4.9% on an allylamine basis.

Workup

  1. customA three-neck flask equipped with a reflux condenser
  2. customreached 85° C.
  3. additionAbout 30 minutes after the addition of the catalyst
  4. customreached 110° C

Sources & evidence

ORD record
ord-ef9b9a7ece684bb88d4293b4500d8cfb
Source dataset
uspto-grants-1989_12
Patent number
US04888436

Reaction notes

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