Allylamine → Allylamine

HRID 477591Notes

Reaction equation

HRID 477591 reaction equation
[CH:1]1[CH2:8][CH2:7]C=CCCC=1.[C]=O.[CH2:11]([O:13][SiH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[CH3:12].[CH2:21]([NH2:24])[CH:22]=[CH2:23]>[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(C)=CC=CC=1>[CH2:21]([NH2:24])[CH:22]=[CH2:23].[NH2:24][CH:8]([CH3:7])[CH2:1][Si:14]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:13][CH2:11][CH3:12]

Participants

8

Reactant 4

HCID 7853AllylamineHCID 8135cis,cis-1,5-CyclooctadieneHCID 13830TriethoxysilaneHCID 178418416HCID 178418416, compound

Product 2

HCID 7853AllylamineHCID 10236113HCID 10236113, compound

Reagents, catalysts & solvents 2

HCID 994031219584-30-6CatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A 200 ml. flask equipped with a stirrer, thermometer, dropping funnel, CO inlet tube and reflux condenser having a CO outlet tube, was flushed with carbon monoxide and charged with 1.9 milligrams of tetrarhodium dodecacarbonyl (2.5×10-6 mole), 0.027 gram of 1,5-cyclooctadiene (2.5×10-4 mole) and 60 ml. of xylene. While passing carbon monooxide through the flask at a rate of 10 ml./min., the mixture was heated to a temperature of 120° C. under stirring. To the mixture a mixture of 41 grams of triethoxy silane (0.25 mole) and 14 grams of allylamine (0.25 mole) was dropwise added over a period of 30 minutes. After the addition of the reactants, the reaction was carried out at a temperature of 120° C. for 2.5 hours under CO flush and stirring. It was revealed by gas chromatography that gamma-aminopropyl triethoxy silane was obtained in a yield of 75% on an allylamine basis, while the yield of beta-aminopropyl triethoxy silane was 7.5% on an allylamine basis.

Workup

  1. customflask equipped with a stirrer
  2. temperaturereflux condenser
  3. customwas flushed with carbon monoxide
  4. additionwas dropwise added over a period of 30 minutes
  5. additionAfter the addition of the reactants
  6. customflush
  7. stirringstirring

Sources & evidence

ORD record
ord-5f93aed616cd4f35ab8e5b0357e71d59
Source dataset
uspto-grants-1989_12
Patent number
US04888436

Reaction notes

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