Toluene → Allylamine

HRID 477590Notes

Reaction equation

HRID 477590 reaction equation
[CH2:1]([O:3][SiH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].[C]=O.[CH2:13]([NH2:16])[CH:14]=[CH2:15].[C:17]1([CH3:23])C=CC=C[CH:18]=1>>[CH2:13]([NH2:16])[CH:14]=[CH2:15].[NH2:16][CH:17]([CH3:23])[CH2:18][Si:4]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7853Allylamine2×HCID 13830TriethoxysilaneHCID 178418416HCID 178418416, compound

Product 2

HCID 7853AllylamineHCID 10236113HCID 10236113, compound

Conditions

Temperature
110 °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 charged with 41 grams of triethoxy silane (0.25 mole), 1.9 milligrams of tetrahodium dodecacarbonyl (2.5×10-6 mole) and 30 ml. of toluene. While passing carbon monoxide through the flask at a rate of 10 ml./min., the mixture was heated to a temperature of 110° C. under stirring. To the mixture 14 grams of allylamine (0.25 mole) was dropwise added in 2 minutes. After the addition of the allylamine the CO flush, heating and stirring were continued for 30 minutes. It was revealed by gas chromatography that gamma-aminopropyl triethoxy silane was obtained in a yield of 62% on an allylamine basis, while the yield of beta-aminopropyl triethoxy silane was 4% on an allylamine basis.

Workup

  1. customflask equipped with a stirrer
  2. temperaturereflux condenser
  3. customflush
  4. temperatureheating
  5. stirringstirring

Sources & evidence

ORD record
ord-c998befab3b54f7ab0b84df8982427cd
Source dataset
uspto-grants-1989_12
Patent number
US04888436

Reaction notes

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