Oxalic Acid → HCID 20042477, compound

HRID 1762109Notes

Reaction equation

HRID 1762109 reaction equation
C1([C:7]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][CH:9]=O)C=CC=CC=1.[CH3:17][C:18]1[CH:30]=[CH:29][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:20][CH:19]=1.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>O1CCCC1.C(OCC)(=O)C.C(C(C)=O)C>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:14]3[CH2:15][N:16]([C:32]4[CH:31]=[CH:9][CH:8]=[CH:7][CH:11]=4)[C:11]4[N:12]([CH:9]=[CH:8][CH:7]=4)[CH:13]=3)[CH2:25][CH2:24]2)=[CH:29][CH:30]=1

Participants

7

Reactant 3

HCID 971Oxalic AcidHCID 7647231-(4-Methylbenzyl)piperazineHCID 54054131HCID 54054131, compound

Product 1

HCID 20042477HCID 20042477, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 6569Methyl Ethyl KetoneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 3-phenyl-3-(2-pyrimidinyl)propenal (1.25 g) in tetrahydrofuran (125 cc) is added to 4-(4-methylbenzyl)piperazine (11.2 g). The solution is stirred and heated to a temperature in the region of 65° C. for 3 hours. After being coiled 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. The residue obtained is dissolved in ethyl acetate (10 cc) and the solution obtained is poured onto silica (25 g) contained in a column 1.5 cm in diameter. Elution is performed with a mixture (750 cc) of ethyl acetate and cyclohexane (50:50 by volume); the corresponding eluates are discarded. Elution is then performed with the same mixture (300 cc) and the corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The oil obtained is dissolved in methyl ethyl ketone (20 cc). Oxalic acid (120 mg) dissolved in methyl ethyl ketone (20 cc) is added and the mixture is stirred for approximately 15 minutes at a temperature in the region of 20° C. The precipitate formed is separated by filtration and then recrystallized in boiling isopropyl alcohol (50 cc). 3-[4-(4-Methylbenzyl)-1-piperazinyl]-1-phenylpyrrolo[1,2-a]pyrimidine oxalate (300 mg), m.p. 205° C., is thereby obtained.

Workup

  1. customAfter being coiled to a temperature in the region of 20° C.
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  3. customThe residue obtained
  4. customthe solution obtained
  5. additionis poured onto silica (25 g)
  6. washElution
  7. washElution
  8. concentrationthe corresponding eluate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  9. customThe oil obtained
  10. additionis added
  11. stirringthe mixture is stirred for approximately 15 minutes at a temperature in the region of 20° C
  12. customThe precipitate formed
  13. customis separated by filtration
  14. customrecrystallized

Sources & evidence

ORD record
ord-a0791d208d7249c2a18cdb0b9a599ae7
Source dataset
uspto-grants-1989_05
Patent number
US04831034

Reaction notes

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