Tert-Butylamine → 3-[4,6-Bis(tert-butylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane

HRID 443762Notes

Reaction equation

HRID 443762 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[N:3]=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([NH:22][C:2]1[N:7]=[C:6]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])[N:5]=[C:4]([N:9]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]([CH2:12][CH2:13]3)[CH2:10]2)[N:3]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 155725793-(4,6-Dichloro-s-triazin-2-yl)-3-azabicyclo[3.2.2]nonane

Product 1

HCID 155725833-[4,6-Bis(tert-butylamino)-s-triazin-2-yl]-3-azabicyclo[3.2.2]nonane

Procedure

3-(4,6-Dichloro-s-triazin-2-yl)-3-azabicyclo[3.2.2]nonane (8.2 g.; 0.03 mole) and 25 ml. (0.24 mole) of t-butylamine is placed in a glass liner in a bomb and then heated in an oil bath maintained at 160°-180° C. for 16 hours. After cooling, the contents of the bomb are rinsed with chloroform and water into a flask and 50 ml. of 10 N NaOH is added. The solution is then evaporated in vacuo and the aqueous solution remaining is extracted with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulfate, filtered through Magnesol® and the Magnesol® washed with chloroform. Removal of solvent in vacuo, column chromatography on silica gel and recrystallization of the pure fractions containing the more polar component from n-heptane gives 4.8 g. of fine colorless crystals, m.p. 217°-222° C.

Workup

  1. temperatureheated in an oil bath
  2. temperaturemaintained at 160°-180° C. for 16 hours
  3. temperatureAfter cooling
  4. washthe contents of the bomb are rinsed with chloroform and water into a flask
  5. additionof 10 N NaOH is added
  6. customThe solution is then evaporated in vacuo
  7. extractionthe aqueous solution remaining is extracted with chloroform
  8. washThe combined chloroform extracts are washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered through Magnesol®
  11. washthe Magnesol® washed with chloroform
  12. customRemoval of solvent in vacuo, column chromatography
  13. customon silica gel and recrystallization of the pure fractions
  14. additioncontaining the more polar component from n-heptane
  15. customgives 4.8 g

Sources & evidence

ORD record
ord-bdcdb6fbbd514823aa074d8c44f3f14e
Source dataset
uspto-grants-1981_04
Patent number
US04261892

Reaction notes

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