HCID 20306038, compound → HCID 20306009, compound

HRID 1732343Notes

Reaction equation

HRID 1732343 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)(=O)C>C(O)C.O.Cl>[NH:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[CH:21][CH:22]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 1

HCID 20306038HCID 20306038, compound

Product 1

HCID 20306009HCID 20306009, compoundYield 9.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-[2-(N-acetyl-4-piperidyloxy)ethoxy]benzamide (4.3 g.) in ethanol (60 ml.), water (30 ml.) and 2 N hydrochloric acid (10 ml.) was heated under reflux for 24 hours then the solvent evaporated in vacuo. The residue was taken up in water and extracted three times with chloroform, the aqueous phase was adjusted to pH 12 with sodium carbonate solution and extracted three times with chloroform. The combined chloroform extracts were discarded, the aqueous phase was saturated with sodium chloride and extracted with chloroform, the chloroform layer dried (Na2SO4), and the solvent evaporated in vacuo to give 4-[2-(4-piperidyloxy)ethoxy]benzamide (0.36 g.). The aqueous phase was concentrated in vacuo and the residual solid extracted with refluxing ethyl acetate (200 ml.).

Workup

  1. temperatureunder reflux for 24 hours
  2. customthe solvent evaporated in vacuo
  3. extractionextracted three times with chloroform
  4. extractionextracted three times with chloroform
  5. extractionextracted with chloroform
  6. dry with materialthe chloroform layer dried (Na2SO4)
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-8ea00480d80b453381454ecc413ea5d3
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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