Hydrochloric Acid → HCID 20339428, compound

HRID 1395448Notes

Reaction equation

HRID 1395448 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH2:13][CH2:14][NH:15][CH2:16][CH:8]1[C:7](=[O:17])[NH:6]2.[CH:20]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)=[CH2:21].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C.CO.C(O)(=O)C>[N:25]1[CH:26]=[CH:27][C:22]([CH2:20][CH2:21][N:15]2[CH2:14][CH2:13][N:9]3[C:10]4[C:5]([NH:6][C:7](=[O:17])[CH:8]3[CH2:16]2)=[CH:4][C:3]([C:2]([F:18])([F:1])[F:19])=[CH:12][CH:11]=4)=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 75024-VinylpyridineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 203394142,3,4,4a-Tetrahydro-8-(trifluoromethyl)-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

Product 1

HCID 20339428HCID 20339428, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 9.0 g. of 2,3,4,4a-tetrahydro-8-trifluoromethyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, 18 ml. of 4-vinylpyridine and 7 ml. of acetic acid was refluxed in 250 ml. of methanol overnight. The solvent was removed and the residue was precipitated with water. The precipitate was filtered and recrystallized from ethanol-water to yield 9.2 g. of the free base, m.p. 204°-206° C. 4 G. of this free base was dissolved in ethanol and treated with dry hydrogen chloride saturated ethanol. The product hydrogen chloride salt was filtered and recrystallized once from i-propanol and once from ethanol to yield 3.4 g. of the dihydrochloride salt of the title compound, m.p. 218°-221° C.

Workup

  1. customThe solvent was removed
  2. customthe residue was precipitated with water
  3. filtrationThe precipitate was filtered
  4. customrecrystallized from ethanol-water
  5. customto yield 9.2 g
  6. filtrationThe product hydrogen chloride salt was filtered
  7. customrecrystallized once from i-propanol and once from ethanol
  8. customto yield 3.4 g

Sources & evidence

ORD record
ord-dcda8105bbff4bb9b867e9acbef41e4d
Source dataset
uspto-grants-1980_05
Patent number
US04203987

Reaction notes

Loading…