Sodium Hydroxide → HCID 18679661, compound

HRID 1633580Notes

Reaction equation

HRID 1633580 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2(O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]=2)[CH:7]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 18679667HCID 18679667, compound

Product 1

HCID 18679661HCID 18679661, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine (0.56 g, 2.5 mmole) in acetic acid (20 mL) at room temperature was added 2 drops of concentrated sulfuric acid and the resulting solution heated to reflux for 2 days. The reaction mixture was cooled to room temperature and diluted with EtOAc (50 mL) and water (50 mL). The solution was basified with 50% NaOH solution until PH=10, the layers separated and the organic layer was washed with brine (25 mL). The combined aqueous layers were extracted three times with EtOAc (3×25 mL), and the combined organic layers were dried over Na2SO4 and concentrated to afford 0.49 g (95% yield) of 4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine as a yellow oil.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux for 2 days
  3. customthe layers separated
  4. washthe organic layer was washed with brine (25 mL)
  5. extractionThe combined aqueous layers were extracted three times with EtOAc (3×25 mL)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c3d297ac217c4db6914458cde3e2b047
Source dataset
uspto-grants-2003_01
Patent number
US06503928B2

Reaction notes

Loading…