Diisopropylamine → 2-Chloro-4-diisopropylamino-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

HRID 345991Notes

Reaction equation

HRID 345991 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Cl:8][C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]([N:16]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3([O:27][CH2:26][CH2:25][O:24]3)[CH2:18][C:17]2([CH3:29])[CH3:28])[N:10]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:8][C:9]1[N:14]=[C:13]([N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[N:12]=[C:11]([N:16]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3([O:27][CH2:26][CH2:25][O:24]3)[CH2:18][C:17]2([CH3:29])[CH3:28])[N:10]=1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 14798Sodium HydroxideHCID 199917702,4-Dichloro-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1yl)-1,3,5-triazine

Product 1

HCID 199917752-Chloro-4-diisopropylamino-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

26.1 g (258 mmol) of diisopropylamine are added with stirring to a solution of 29.9 g (86 mmol) of the product from Example 17 in 100 ml of toluene. The mixture is heated to reflux and kept at this temperature for 24 hours. After cooling, a solution of 4.1 g of NaOH in 21 ml of water is added. The solid product is filtered off and recrystallized from 25 ml of toluene. A yellowish powder which melts at 179°-184° is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. filtrationThe solid product is filtered off
  5. customrecrystallized from 25 ml of toluene
  6. customA yellowish powder which melts at 179°-184° is obtained

Sources & evidence

ORD record
ord-ef47917044984126b629083716335d00
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

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