Allylamine → 2,2,4-Trimethyl-1-allyl-1-aza-2-silacyclopentane

HRID 2255253Notes

Reaction equation

HRID 2255253 reaction equation
Cl[Si:2]([CH3:9])([CH3:8])[CH2:3][CH:4]([CH3:7])[CH2:5]Cl.[CH2:10]([NH2:13])[CH:11]=[CH2:12]>>[CH3:8][Si:2]1([CH3:9])[CH2:3][CH:4]([CH3:7])[CH2:5][N:13]1[CH2:10][CH:11]=[CH2:12]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 86665Chloro(3-chloro-2-methylpropyl)dimethylsilane

Product 1

HCID 191071842,2,4-Trimethyl-1-allyl-1-aza-2-silacyclopentane

Procedure

The 2,2,4-trimethyl-1-allyl-1-aza-2-silacyclopentane was prepared as follows. Chlorodimethyl(3-chloro-2-methylpropyl)silane (100 g, 0.54 mol) was slowly added to 211.73 g (3.71 mol, 6.87 eq) of undistilled allyl amine resulting in an exothermic reaction. This reaction mixture was stirred at room temperature for 15 hours, heated to reflux at atmospheric pressure for 72 hours, and heated to 120° C. under about 50 psig pressure for 16 hours. The following GC-MS ratios shown in the Table exemplified the reactions progression and the spectra observed were as shown.

Workup

  1. temperatureheated
  2. temperatureto reflux at atmospheric pressure for 72 hours
  3. temperatureheated to 120° C. under about 50 psig pressure for 16 hours

Sources & evidence

ORD record
ord-5d92a4744908400ea3194fb3c50edd22
Source dataset
uspto-grants-1993_08
Patent number
US05239099

Reaction notes

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