Oxalic Acid → HCID 13516759, compound

HRID 1285341Notes

Reaction equation

HRID 1285341 reaction equation
[H-].[Na+].[OH:3][CH:4]([CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[CH3:31])[CH2:20][CH2:19]1)[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[CH2:32](Br)[CH:33]=[CH2:34].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].C(OC(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[CH2:34]([O:3][CH:4]([CH2:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[CH3:31])[CH2:20][CH2:19]1)[CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])[CH:33]=[CH2:32]

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 7841Allyl bromideHCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 20248979HCID 20248979, compound

Product 1

HCID 13516759HCID 13516759, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

55% Sodium hydride (0.65 g) was suspended in anhydrous dioxane (30 ml), followed by dropwise addition of N-[2-hydroxy-3-{4-(2,4-dimethylphenyl)piperazin-1-yl}propyl]-phthalimide (4.7 g) dissolved in dioxane (50 ml) under nitrogen gas stream and at room temperature. The resulting mixture was heated to 60° C. and stirred for 1 hour. Then, allyl bromide (1.8 g) was dropped slowly into the mixture at 40° C. and the thus formed mixture was stirred for 3 hours over a water bath at 75° C. The reaction mixture was thereafter cooled, ice water was added thereto, and it was then extracted with ether. After washing the extract twice with water, it was dried with anhydrous magnesium sulfate. The resulting mixture was filtered and the filtrate was concentrated. After washing out the mineral oil, derived from sodium hydride, with n-hexane, the residue was dissolved in ethyl acetate, followed by addition of a solution which had been obtained by dissolving oxalic acid (1.2 g) in ethyl acetate. After heating the resulting mixture, a small amount of IPE (isopropyl ether) was added. The thus obtained mixture was allowed to cool. Precipitated crystals were collected by filtration to obtain the desired compound (4.3 g; yield 69%).

Workup

  1. customat room temperature
  2. stirringthe thus formed mixture was stirred for 3 hours over a water bath at 75° C
  3. temperatureThe reaction mixture was thereafter cooled
  4. extractionit was then extracted with ether
  5. washAfter washing the
  6. extractionextract twice with water, it
  7. dry with materialwas dried with anhydrous magnesium sulfate
  8. filtrationThe resulting mixture was filtered
  9. concentrationthe filtrate was concentrated
  10. washAfter washing out the mineral oil
  11. dissolutionthe residue was dissolved in ethyl acetate
  12. additionfollowed by addition of a solution which
  13. customhad been obtained
  14. temperatureAfter heating the resulting mixture
  15. temperatureto cool
  16. customPrecipitated crystals
  17. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-31842033312d4477a79050383fcbbf4e
Source dataset
uspto-grants-1986_01
Patent number
US04567180

Reaction notes

Loading…