O-Xylene → HCID 69885104, compound

HRID 1059328Notes

Reaction equation

HRID 1059328 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4](O)=O.[C:9]1(C)C(C)=CC=CC=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27](CC=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>N1CCCCC1.O.C(OCC)C>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH:4]=[CH:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 3

HCID 7237O-XyleneHCID 444266Maleic AcidHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 69885104HCID 69885104, compound

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

3.12 g of maleic acid and one drop of piperidine were added to 50 ml of xylene and the resulting mixture was heated under reflux for 30 minutes. After adding 2.27 g of [1-(tert-butoxycarbonyl)piperidin-4-yl]acetaldehyde, the resulting mixture was heated under reflux for 2 hours and 20 minutes while eliminating water with a Dean Stark trap. Then the reaction mixture was distributed into diethyl ether and water, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The obtained residue was dissolved in 150 ml of diethyl ether and treated with a solution of diazomethane in diethyl ether. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.71 g of the title compound as an oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for 2 hours and 20 minutes
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. dissolutionThe obtained residue was dissolved in 150 ml of diethyl ether
  10. additiontreated with a solution of diazomethane in diethyl ether
  11. distillationAfter distilling off the solvent under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d0fa9e9270884581b4bfdf90692ec6c5
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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