Sodium Hydroxide → 2,3-Dihydro-5-[1-oxo-3-(piperidin-4-yl)propyl]benzofuran

HRID 327404Notes

Reaction equation

HRID 327404 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:21][CH2:20][CH2:19][C:18]=3[CH:22]=2)=[O:13])[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[O:13]=[C:12]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][CH2:20][CH2:19][C:18]=2[CH:22]=1)[CH2:11][CH2:10][CH:7]1[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 191084645-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-2,3-dihydrobenzofuran

Product 1

HCID 191084552,3-Dihydro-5-[1-oxo-3-(piperidin-4-yl)propyl]benzofuranYield 100.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 30 ml of concentrated hydrochloric acid was added 5.00 g of 5-[3-(1-acetylpiperidin-4-yl)-1-oxopropyl]-2,3-dihydrobenzofuran, and the mixture was refluxed for 14 hours. The reaction mixture was left standing for cooling and then made basic with a dilute aqueous solution of sodium hydroxide, followed by extraction with methylene chloride. Organic layers were combined and dried over anhydrous sodium sulfate, then the solvent was distilled off to leave 4.31 g (100%) of 2,3-dihydro-5-[1-oxo-3-(piperidin-4-yl)propyl]benzofuran (4). The solid matter thus obtained was dissolved in methanol, treated with hydrogen chloride and recrystallized from methanol--ethyl acetate to give colorless needles, m.p. 203°-205° C. (decomp.)

Workup

  1. temperaturethe mixture was refluxed for 14 hours
  2. waitThe reaction mixture was left
  3. temperaturefor cooling
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-851d009da0a8402bbcee7025bacdf664
Source dataset
uspto-grants-1993_12
Patent number
US05273974

Reaction notes

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