Tert-Butylamine → HCID 14875919, compound

HRID 978666Notes

Reaction equation

HRID 978666 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH:17](O)[CH3:18])([CH3:9])([CH3:8])[CH3:7]>C1(C)C=CC=CC=1>[C:1]([NH:5][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][NH:10][C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 131715135HCID 131715135, compound

Product 1

HCID 14875919HCID 14875919, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

To a 300 ml stainless steel, stirred autoclave there was added 21 g of tertiarybutylamine, 20 g of tertiarybutylaminoethoxyethoxyethanol, 0.6 g of Ni-Al2O3 -SiO2 catalyst (Harshaw NI-5132P), and 50 ml of toluene. The autoclave containing the reactants was heated to 200° C. under autogenous pressure (180 psi) for 6 hours. The contents were cooled, removed and filtered. The autoclave and filtercake were washed with additional toluene. G.C. analysis revealed that the product was comprised of about 91 wt. % 1,2-bis-(tertiarybutylaminoethoxy) ethane and less than about 5 wt. % tertiarybutylaminoethoxyethoxyethanol. Vacuum distillation gave 17.3 g of 1,2-bis-(tertiarybutylaminoethoxy) ethane, having a boiling point of 125°-128° C./3 mm.

Workup

  1. additionThe autoclave containing the reactants
  2. temperatureThe contents were cooled
  3. customremoved
  4. filtrationfiltered
  5. washThe autoclave and filtercake were washed with additional toluene
  6. distillationVacuum distillation

Sources & evidence

ORD record
ord-5490e6504ad94b7794185ef206505bff
Source dataset
uspto-grants-1987_05
Patent number
US04665195

Reaction notes

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