Triethylamine → HCID 20339405, compound

HRID 1395452Notes

Reaction equation

HRID 1395452 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]Cl)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CC(C)=O>[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]([CH2:23][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

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 745714-(Chloromethyl)pyridineHCID 20339413HCID 20339413, compound

Product 1

HCID 20339405HCID 20339405, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2 g. (0.008 mole) of 8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one and 1.6 g. (0.01 mole) of 4-picolyl chloride, 3.5 g. of potassium carbonate and 0.5 ml. of triethylamine was stirred and refluxed in 100 ml. of acetone for 48 hours, cooled and filtered. The solvent was removed under reduced pressure. The residue was dissolved in ethanol and treated with dry hydrogen chloride saturated ether. The product hydrochloride was filtered and recrystallized from ethanol-water to yield 1.25 g. of the title compound as the dihydrochloride, m.p. 269°-272° C.

Workup

  1. temperaturerefluxed in 100 ml
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol
  6. additiontreated with dry hydrogen chloride saturated ether
  7. filtrationThe product hydrochloride was filtered
  8. customrecrystallized from ethanol-water
  9. customto yield 1.25 g

Sources & evidence

ORD record
ord-5419bb080c994bcfaa44124319d4dc88
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

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