Hydrochloric Acid → HCID 66643096, compound

HRID 869259Notes

Reaction equation

HRID 869259 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:21][CH2:20][C:15]2(OCC[O:16]2)[CH2:14][CH2:13]1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66642824HCID 66642824, compound

Product 1

HCID 66643096HCID 66643096, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 8-(2-methoxy-5-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane (Preparation Example 495) (795 mg) and dioxane (16 mL), 4M hydrochloric acid (6.8 mL) was added and stirred overnight at 80° C. The reaction liquid was concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate was added to the concentrate. The concentrate was extracted with chloroform and then washed with saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane) to give 1-(2-methoxy-5-nitrophenyl)piperidin-4-one (296 mg).

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure, and saturated aqueous sodium hydrogen carbonate
  4. additionwas added to the concentrate
  5. extractionThe concentrate was extracted with chloroform
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane)

Sources & evidence

ORD record
ord-f51c9df401a84c09b958a98594352a57
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

Loading…