Dibutylamine → 2,4-Bis-dibutylamino-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

HRID 345985Notes

Reaction equation

HRID 345985 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]2([CH3:18])[CH3:17])[N:3]=1.[CH2:19]([NH:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>C1(C)C(C)=CC=CC=1.O>[CH2:19]([N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[C:2]1[N:7]=[C:6]([N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:20][CH2:21][CH3:22])[N:5]=[C:4]([N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]2([CH3:18])[CH3:17])[N:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 8148DibutylamineHCID 14798Sodium HydroxideHCID 199917662,4-Dichloro-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Product 1

HCID 199917512,4-Bis-dibutylamino-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

57.8 g of 2,4-dichloro-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine are suspended in 200 ml of xylene at room temperature. 25.8 g of dibutylamine are added dropwise to this during the course of 15 minutes, the temperature climbing to 40°. A solution of 8.87 g of sodium hydroxide in 40 ml of water is added to the reaction mixture in about 15 minutes and it is subsequently stirred at 60° for 2 hours. The aqueous phase is then separated off and 28.4 g of dibutylamine and a solution of 9.6 g of sodium hydroxide in 20 ml of water is added to the clear organic phase. The mixture is then heated in a water separator until an internal temperature of about 135° is reached and is then stirred for 12 hours at this temperature. The contents of the flask are cooled to 90°, a solution of 3 g of sodium hydroxide in 100 ml of water is added and the mixture is vigorously stirred at 90° for 30 minutes. The aqueous phase is then separated off, the xylene solution is washed five times, each with 100 ml of water, and evaporated in vacuo. The yellowish, oily residue is distilled in a high vacuum. 2,4-Bis-dibutylamino-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine is obtained as a colorless oil having a boiling point of 173° at 6.5 Pa.

Workup

  1. customclimbing to 40°
  2. customThe aqueous phase is then separated off
  3. addition28.4 g of dibutylamine and a solution of 9.6 g of sodium hydroxide in 20 ml of water is added to the clear organic phase
  4. temperatureThe mixture is then heated in a water separator until an internal temperature of about 135°
  5. stirringis then stirred for 12 hours at this temperature
  6. temperatureThe contents of the flask are cooled to 90°
  7. additiona solution of 3 g of sodium hydroxide in 100 ml of water is added
  8. stirringthe mixture is vigorously stirred at 90° for 30 minutes
  9. customThe aqueous phase is then separated off
  10. washthe xylene solution is washed five times
  11. customeach with 100 ml of water, and evaporated in vacuo
  12. distillationThe yellowish, oily residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-6bdf50270bfc430a892cd9c78e5c6bb4
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

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