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Hydrochloric Acid → HCID 20339406, compound

HRID 1395453
Notes
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Reaction equation

HRID 1395453 reaction equation
Cl.[CH2:2]1[N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[CH:6]2[CH2:5][NH:4][CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[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>[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][N:4]2[CH2:3][CH2:2][N:7]3[C:8]4[C:13]([NH:14][C:15](=[O:16])[CH:6]3[CH2:5]2)=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 109539414-(4-Chlorobutyl)pyridineHCID 18377410HCID 18377410, compound

Product 1

HCID 20339406HCID 20339406, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent
HCID 702EthanolSolvent
HCID 8471TriethylamineSolvent

Procedure

A solution of 6.2 g. (0.03 mole) of 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, hydrochloride, 7 g. (0.04 mole) of 4-(4-pyridyl)-1-chlorobutane, 10 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 48 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 3.2 g. of free base. 3 G. of the above 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 3.2 g. of the title compound as the dihydrochloride salt, m.p. 281°-283° 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 3.2 g
  13. filtrationThe product hydrochloride was filtered
  14. customrecrystallized from methanol
  15. customto give 3.2 g

Sources & evidence

ORD record
ord-9519b5cb1e74496091edb226acc00108
Source dataset
uspto-grants-1980_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04203987

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes