Sodium hydride → HCID 131711265, compound

HRID 1764332Notes

Reaction equation

HRID 1764332 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([CH3:14])=[CH:4][N:3]=1.C1(C2[N:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][CH:23]([CH2:29][OH:30])[O:22]2)C=CC=CC=1.[H-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[CH:26]([NH:25][CH2:24][CH:23]([OH:22])[CH2:29][O:30][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][C:5]([CH3:14])=[CH:4][N:3]=1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125661982-Phenyl-3-isopropyl-5-hydroxymethyloxazolidineHCID 570620344-(3-Chloro-6-methylpyrazin-2-yl)morpholine

Product 1

HCID 131711265HCID 131711265, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

10.7 g of 2-chloro-3-morpholinyl-5-methyl-pyrazine and 16.6 g of 2-phenyl-3-isopropyl-5-hydroxymethyloxazolidine are dissolved in 130 ml of hexamethylphosphoric acid triamide. 3.6 g of a 50% strength suspension of sodium hydride in paraffin oil are introduced into this solution over the course of 30 minutes at 0°-5° C., whilst stirring. The mixture is then stirred for 1 hour at 0°-5° C. and 24 hours at room temperature. The reaction mixture is then poured onto 500 ml of ice water and extracted by shaking with ether. The ether extracts are washed with water and evaporated in a waterpump vacuum. The residue is taken up in 200 ml of 1 N sulphuric acid and the reaction mixture is stirred for 15 hours at room temperature and then extracted by shaking with ether. The acid aqueous phase is rendered alkaline with concentrated sodium hydroxide solution and is then extracted by shaking with ether. The ether extracts are washed with water, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue crystallises from etherpentane. 2-(3'-Isopropylamino-2'-hydroxy-propoxy)-3-morpholinyl-5-methyl-pyrazine, melting point 77°-78° C., is thus obtained.

Workup

  1. additionare introduced into this solution over the course of 30 minutes at 0°-5° C.
  2. stirringThe mixture is then stirred for 1 hour at 0°-5° C. and 24 hours at room temperature
  3. extractionextracted
  4. stirringby shaking with ether
  5. washThe ether extracts are washed with water
  6. customevaporated in a waterpump vacuum
  7. stirringthe reaction mixture is stirred for 15 hours at room temperature
  8. extractionextracted
  9. stirringby shaking with ether
  10. extractionis then extracted
  11. stirringby shaking with ether
  12. washThe ether extracts are washed with water
  13. dry with materialdried over sodium sulphate
  14. customevaporated in a waterpump vacuum
  15. customThe residue crystallises from etherpentane

Sources & evidence

ORD record
ord-bc908eeff8b5419f8de84c61ac0b19b7
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

Loading…