Oxalic Acid → HCID 20042478, compound

HRID 1762108Notes

Reaction equation

HRID 1762108 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:15]1([C:21]([C:25]2[CH:30]=[N:29][CH:28]=[CH:27][N:26]=2)=CC=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:31](C(C)=O)[CH3:32].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>O1CCCC1.C(Cl)Cl>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:28]3[N:29]=[C:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:25]4[N:26]([CH:31]=[CH:32][CH:30]=4)[CH:27]=3)[CH2:9][CH2:8]2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 6569Methyl Ethyl Ketone2×HCID 7647231-(4-Methylbenzyl)piperazineHCID 57293313HCID 57293313, compound

Product 1

HCID 20042478HCID 20042478, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
66 °C

Procedure

A solution of 1-(4-methylbenzyl)piperazine (9.5 g) in tetrahydrofuran (50 cc) is added in the course of 10 minutes at a temperature in the region of 20° C. to a stirred solution of 3-phenyl-3-pyrazinylpropenal (1 g) in tetrahydrofuran (50 cc), and the mixture is left with stirring for 3 hours at a temperature in the region of 66° C. After the solution is cooled to a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. A residue is obtained which is dissolved in methylene chloride (10 cc). The solution obtained is poured onto silica (200 g) contained in a column 3.5 cm in diameter. Elution is performed with a mixture (500 cc) of methylene chloride and methanol (99.5:0.5 by volume) and the corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The oil obtained is dissolved in boiling methyl ethyl ketone (20 cc). A solution of oxalic acid (0.25 g) in boiling methyl ethyl ketone (20 cc) is added. After the mixture is cooled to a temperature in the region of 20° C., the precipitate formed is separated by filtration and then recrystallized in boiling isopropyl alcohol (80 cc). 3-[4-(4-Methylbenzyl)-1-piperazinyl]-1-phenylpyrrolo[1,2-a]pyrazine oxalate (0.4 g), m.p. 128° C., is thereby obtained.

Workup

  1. waitthe mixture is left
  2. temperatureAfter the solution is cooled to a temperature in the region of 20° C.
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  4. customA residue is obtained which
  5. customThe solution obtained
  6. additionis poured onto silica (200 g)
  7. washElution
  8. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  9. customThe oil obtained
  10. dissolutionis dissolved
  11. additionis added
  12. temperatureAfter the mixture is cooled to a temperature in the region of 20° C.
  13. customthe precipitate formed
  14. customis separated by filtration
  15. customrecrystallized

Sources & evidence

ORD record
ord-85709f0520b54d19a19fd3d4ffbd76fa
Source dataset
uspto-grants-1989_05
Patent number
US04831034

Reaction notes

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