Hydrochloric Acid → N-(o-(2,2,2-Trifluoroethoxy)phenyl)-4-piperidone

HRID 842795Notes

Reaction equation

HRID 842795 reaction equation
C1O[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:7][CH2:6]2)[O:4]C1C.Cl>C(O)(=O)C.O>[F:22][C:19]([F:20])([F:21])[CH2:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57019377N-(2-(2,2,2-Trifluoroethoxy)phenyl)-4-piperidone propylene ketal

Product 1

HCID 22615386N-(o-(2,2,2-Trifluoroethoxy)phenyl)-4-piperidone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 51 (410 mg, 1.23 mmol) in acetic acid (20 mL), water (20 ml), and concetrated HCl (5 mL) was heated in an oil bath (60° C.) overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 4 mm, 10% EtOH-90% CHCl3) afforded the title compound (52)

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  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-273c4be4a94a4f7cb10e8449a1f55de3
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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