Hydrochloric Acid → 2,3,4,4a-Tetrahydro-6-Methyl-3-[(4-Pyridinyl)Methyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

HRID 1395455Notes

Reaction equation

HRID 1395455 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH2:12][CH2:13][NH:14][CH2:15][CH:4]2[C:3]1=[O:16].Cl.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.CC(C)=O.C(N(CC)CC)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH2:12][CH2:13][N:14]([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH2:15][CH:4]2[C:3]1=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 183773372,3,4,4a-Tetrahydro-6-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

Product 1

HCID 203394082,3,4,4a-Tetrahydro-6-Methyl-3-[(4-Pyridinyl)Methyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6 g. (0.03 mole) of 2,3,4,4a-tetrahydro-6-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, 5 g. (0.03 mole) of 4-picolyl chloride hydrochloride, 10 g. of potassium carbonate and 0.5 ml. of triethylamine was stirred and refluxed in 200 ml. of acetone overnight, cooled and filtered. The solvent was removed and the residue was dissolved in methylene chloride. This solution was washed with water and brine, dried over magnesium sulfate and filtered. The solvent was removed and the residue was chromatographed on 460 g. of Silicar, CC-7. Fractions eluted with 10% methanol in ethyl acetate afforded the product as a free base. This free base was dissolved in ethanol and treated with dry hydrogen chloride saturated ether. The product hydrochloride was filtered and recrystallized from methanol to yield 5.2 g. of the title compound as the dihydrochloride salt, m.p. 252°-254.5° C.

Workup

  1. temperaturerefluxed in 200 ml
  2. filtrationfiltered
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThis solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed
  9. customthe residue was chromatographed on 460 g
  10. washFractions eluted with 10% methanol in ethyl acetate
  11. customafforded the product as a free base
  12. filtrationThe product hydrochloride was filtered
  13. customrecrystallized from methanol
  14. customto yield 5.2 g

Sources & evidence

ORD record
ord-2793b74a74ff41b4886a94d300245c9e
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

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