Morpholine → N-Cyclopropyl-6-(morpholin-4-yl)-4-propyl-1,3,5-triazin-2(1H)-imine

HRID 256707Notes

Reaction equation

HRID 256707 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[N:13]=[C:12]([NH:14][CH:15]2[CH2:17][CH2:16]2)[N:11]=[C:10]([CH2:18][CH2:19][CH3:20])[N:9]=1>O1CCOCC1>[CH:15]1([NH:14][C:12]2[N:13]=[C:8]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[N:11]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 18965210HCID 18965210, compound

Product 1

HCID 192460N-Cyclopropyl-6-(morpholin-4-yl)-4-propyl-1,3,5-triazin-2(1H)-imineYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

45 ml (0.45 mole) of morpholine dissolved in 200 ml of dioxane are added to a solution containing 43 g (0.163 mole) of 2-chloro-4-cyclopropylamino-6-n-propyl-1,3,5-triazine in 300 ml of dioxane, while maintaining the mixture at room temperature. After the addition, the mixture is heated under reflux for one to two hours. The reaction mixture is then allowed to return to room temperature and the precipitate is filtered off. The filtrate is concentrated and the residue is redissolved in dichloromethane. The solution is washed with water. The organic phase is separated off and dried over sodium sulfate. The solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica (eluent: 98.5:1.5 (v/v) dichloromethane-ethanol) and the product is finally recrystallized from diethyl ether. 36.2 g of 2-cyclopropylamino-4-morpholino-6-n-propyl-1,3,5-triazine are obtained. Yield: 85%. M.P.: 104° C.

Workup

  1. additionare added to a solution
  2. additionAfter the addition
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for one to two hours
  5. customto return to room temperature
  6. filtrationthe precipitate is filtered off
  7. concentrationThe filtrate is concentrated
  8. dissolutionthe residue is redissolved in dichloromethane
  9. washThe solution is washed with water
  10. customThe organic phase is separated off
  11. dry with materialdried over sodium sulfate
  12. customThe solvent is evaporated under reduced pressure
  13. customThe residue is purified by chromatography on silica (eluent: 98.5:1.5 (v/v) dichloromethane-ethanol)
  14. customthe product is finally recrystallized from diethyl ether

Sources & evidence

ORD record
ord-50096cab099648d1a08db906667096b3
Source dataset
uspto-grants-1993_11
Patent number
US05258513

Reaction notes

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