Acetic Anhydride → HCID 14931743, compound

HRID 1252056Notes

Reaction equation

HRID 1252056 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH2:11]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19](=[O:21])[CH3:20])[CH2:11]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 14931742HCID 14931742, compound

Product 1

HCID 14931743HCID 14931743, compound

Procedure

A mixture of 3-(1-acetyl-4-piperidyl)indoline (41.1 g) and acetic anhydride (300 ml) was refluxed for 3 hours. The excess acetic anhydride was distilled off under reduced pressure and the residue was dissolved in ethyl acetate (500 ml). The solution was washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml), water (100 ml) and a saturated aqueous solution of sodium chloride successively and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel, elution being carried out with a mixture of chloroform and methanol (40:1 V/V) to give 3-(1-acetyl-4-piperidyl)-1-acetylindoline (32 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationThe excess acetic anhydride was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (500 ml)
  4. washThe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml), water (100 ml)
  5. dry with materiala saturated aqueous solution of sodium chloride successively and dried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washthe residue was subjected to column chromatography on silica gel, elution
  8. additionbeing carried out with a mixture of chloroform and methanol (40:1 V/V)

Sources & evidence

ORD record
ord-dd990ae3c3fb4d0d97f2f6fd305aec25
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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