Hydrochloric Acid → HCID 20339421, compound

HRID 1395454Notes

Reaction equation

HRID 1395454 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][NH:14][CH2:15][CH:7]1[C:6](=[O:16])[NH:5]2.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>C(O)C.CC(C)=O.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][N:14]([CH2:26][CH2:25][CH2:24][CH2:23][C:20]3[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=3)[CH2:15][CH:7]1[C:6](=[O:16])[NH:5]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109539414-(4-Chlorobutyl)pyridineHCID 20339413HCID 20339413, compound

Product 1

HCID 20339421HCID 20339421, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4.2 g. (0.02 mole) of 8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, 7 g. (0.04 mole) of 4-(4-pyridyl)-1-chlorobutane, 8 g. of potassium carbonate, 5 g. of potassium iodide, and 0.5 ml. of triethylamine was stirred and refluxed in 200 ml. of acetone for 72 hours, 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 500 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 give 2.3 g. of the title compound as the dihydrochloride salt, m.p. 262°-264° C.

Workup

  1. temperaturerefluxed in 200 ml
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was removed
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washThis solution was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe residue was chromatographed on 500 g
  11. washFractions eluted with 10% methanol in ethyl acetate
  12. customafforded the product as a free base
  13. filtrationThe product hydrochloride was filtered
  14. customrecrystallized from methanol
  15. customto give 2.3 g

Sources & evidence

ORD record
ord-2fda4a9d47d64f8c95e0159097877108
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

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