Benzene → HCID 13576941, compound

HRID 544710Notes

Reaction equation

HRID 544710 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1C=CC=C[CH:3]=1.[NH2+:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:3][CH:2]1[C:18]2[CH:19]=[CH:20][C:21]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:22][C:17]=2[O:9][C:1]1=[O:8]

Participants

4

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 573505385285-31-4

Product 1

HCID 13576941HCID 13576941, compound

Procedure

A mixture of 9.1 g (0.05 mole) of 4-methyl-3-(3-oxobutyl)-maleic acid anhydride and 11 g (0.053 mole) of piperidinium benzoate in 200 ml of benzene is heated under reflux for 48 hours using a water separator. The benzene is removed in vacuo and the residue that remains is partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product remaining after drying and after removal of the methylene chloride is chromatographed over silica gel with petroleum ether/ether. Subsequent recrystallisation from ether/petroleum ether yields 3-methyl-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 78°-80° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customThe benzene is removed in vacuo
  4. customthe residue that remains is partitioned between methylene chloride and saturated sodium bicarbonate solution
  5. customafter drying
  6. customafter removal of the methylene chloride
  7. customis chromatographed over silica gel with petroleum ether/ether
  8. customSubsequent recrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-12a87530bdfa40b2a7a248737dcf5c4b
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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