Potassium Carbonate → HCID 20339425, compound

HRID 1395450Notes

Reaction equation

HRID 1395450 reaction equation
[CH2:1]1[N:6]2[C:7]3[C:12]([NH:13][C:14](=[O:15])[CH:5]2[CH2:4][NH:3][CH2:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.Cl.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:3]2[CH2:2][CH2:1][N:6]3[C:7]4[C:12]([NH:13][C:14](=[O:15])[CH:5]3[CH2:4]2)=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 1563622,3,4,4a-Tetrahydro-1H-pyrazino(1,2a)quinoxalin-5-(6H)one

Product 1

HCID 20339425HCID 20339425, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one 6.1 g. (0.03 mole) and 4.92 g. (0.03 mole) of 4-picolyl chloride hydrochloride, 10 g. of potassium carbonate, 0.5 ml. of tirethylamine in 200 ml. of acetone was refluxed for 40 hours with stirring. The reaction mixture was allowed to cool and the precipitate was filtered and washed with acetone. The acetone was removed under reduced pressure and the oily residue was dissolved in methylene chloride. This solution was washed with water, dried over magnesium sulfate, filtered and the solvent removed. The residue was dissolved in ethanol and treated with dry hydrogen chloride. The product hydrogen chloride was filtered and recrystallized from methanol to give 2 g. of the title compound as the dihydrochloride salt, m.p. 253°-255° C.

Workup

  1. temperatureto cool
  2. filtrationthe precipitate was filtered
  3. washwashed with acetone
  4. customThe acetone was removed under reduced pressure
  5. dissolutionthe oily residue was dissolved in methylene chloride
  6. washThis solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. dissolutionThe residue was dissolved in ethanol
  11. additiontreated with dry hydrogen chloride
  12. filtrationThe product hydrogen chloride was filtered
  13. customrecrystallized from methanol
  14. customto give 2 g

Sources & evidence

ORD record
ord-940c2a926b1f4b2594d976d60f9e660f
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

Loading…