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

HRID 345997Notes

Reaction equation

HRID 345997 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl:9][C:10]1[N:15]=[C:14](Cl)[N:13]=[C:12]([N:17]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:19][C:18]2([CH3:30])[CH3:29])[N:11]=1>O.C1(C)C=CC=CC=1>[Cl:9][C:10]1[N:15]=[C:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:13]=[C:12]([N:17]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:19][C:18]2([CH3:30])[CH3:29])[N:11]=1

Participants

6

Reactant 3

HCID 8083Morpholine2×HCID 14798Sodium Hydroxide2×HCID 199917702,4-Dichloro-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1yl)-1,3,5-triazine2×

Product 1

HCID 199917602-Chloro-4-morpholino-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

3.8 g of morpholine and, 15 minutes later, a solution of 1.7 g of NaOH in 5 ml of water are added to a solution of 30 g of 2,4-dichloro-6-(4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine (product from Example 17) in 100 ml of toluene. The mixture is then warmed to 6020 and after 45 minutes a further 3.8 g of morpholine and 1.7 g of NaOH in 5 ml of water are added. After a further 1.5 hours, the reaction has ended. After cooling and adding 200 ml of toluene, the phases are separated. The organic phase is dried over Na2SO4 and evaporated. Recrystallizing from acetonitrile leads to the compound of the above structure which melts at 154°-156° (white powder).

Workup

  1. additionare added
  2. temperatureAfter cooling
  3. customthe phases are separated
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customevaporated
  6. customRecrystallizing from acetonitrile leads to the compound of the above structure which melts at 154°-156° (white powder)

Sources & evidence

ORD record
ord-766a6fc445b14e6f83e1a5aa8451b644
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

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