Anthranilic Acid → HCID 21699698, compound

HRID 1597288Notes

Reaction equation

HRID 1597288 reaction equation
[C:1](O)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)([Cl:27])=O>>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]2[N:4]=[C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]3=[C:1]([Cl:27])[C:20]=2[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 192201-Benzyl-4-piperidoneHCID 24813Phosphorus oxychloride

Product 1

HCID 21699698HCID 21699698, compoundYield 60.1%

Procedure

Anthranilic acid (9.6 g, 70 mmol) and 1-benzyl-4-piperidone (13.2 g, 70 mmol) were suspended in phosphorus oxychloride (65.2 ml, 700 mmol), and the suspension was heated under reflux for 4 hours. The excess phosphorus oxychloride was removed by distillation and the concentrated residue was carefully added to 28% aqueous ammonia under ice-cooling and extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate/methanol=30:10:1) to obtain the desired compound (13 g, 60%) as a light-yellowish-white substance.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 4 hours
  3. customThe excess phosphorus oxychloride was removed by distillation
  4. additionthe concentrated residue was carefully added to 28% aqueous ammonia under ice-
  5. temperaturecooling
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate/methanol=30:10:1)

Sources & evidence

ORD record
ord-0eee6417a3514571aa0cc3a7ded6620e
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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