Sodium Hydroxide → HCID 57438801, compound

HRID 2263512Notes

Reaction equation

HRID 2263512 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1(O)[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1.[OH-].[Na+]>>[F:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH:13]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 68779159HCID 68779159, compound

Product 1

HCID 57438801HCID 57438801, compoundYield 52.6%

Procedure

A solution of 4-[2-fluoro-3-(trifluoromethyl)phenyl]-1-methylpiperidin-4-ol (1.2 g, 4.33 mmol) in polyphosphoric acid (4 ml) was heated at 100° C. for 2 h. The mixture was poured on to ice and was basified with an aqueous sodium hydroxide solution (15%). The mixture was extracted with ethylacetate (3×50 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (ethylacetate/methanol, 1:1) to give the title compound (0.59 g). MS m/z (rel. intensity, 70 eV) 259 (M+, bp), 258 (66), 147 (74), 146 (27), 96 (52).

Workup

  1. additionThe mixture was poured on to ice
  2. extractionThe mixture was extracted with ethylacetate (3×50 ml)
  3. dry with materialthe combined organic phases was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-e82cec5df6674035804d1e9ef9cab842
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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