Hydrochloric Acid → 1-(2-methoxyphenyl)piperidin-4-one

HRID 842777Notes

Reaction equation

HRID 842777 reaction equation
C1O[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])[CH2:6][CH2:5]2)[O:3]C1.Cl>C(O)(=O)C.O>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18727003HCID 18727003, compound

Product 1

HCID 226154131-(2-methoxyphenyl)piperidin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 19 (570 mg, 2.28 mmol) in acetic acid (20 mL), water (20 ml), and concetrated HCl (5 mL) was heated in an oil bath (50° C.) overnight. The solvent was removed in vacuo and the residue dissolved in ether and sodium carbonate solution. The aqueous layer was extracted with two additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 2 mm, CHCl3) afforded the title compound (20)

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ether
  3. extractionThe aqueous layer was extracted with two additional portions of ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78b0210f7a644b369c133b0e1ecf163c
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

Loading…