Sodium Hydroxide → HCID 67532346, compound

HRID 1879011Notes

Reaction equation

HRID 1879011 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]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]1.[OH-].[Na+]>FC(F)(F)C(O)=O>[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]([CH2:18][CH2:19][CH3:20])[CH2:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11709279HCID 11709279, compound

Product 1

HCID 67532346HCID 67532346, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-[2-fluoro-3-(trifluoromethyl)phenyl]-1-propylpiperidin-4-ol (8.0 g, 26 mmol) in trifluoroacetic acid (80 ml) was heated at reflux for 20 h. The mixture was poured on to ice and was basified with 10 M sodium hydroxide. The mixture was extracted with ethylacetate (3×100 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 (5.6 g). MS m/z (rel. intensity, 70 eV) 287 (M+, 22), 259 (16), 258 (bp), 177 (10), 147 (10).

Workup

  1. temperatureat reflux for 20 h
  2. additionThe mixture was poured on to ice
  3. extractionThe mixture was extracted with ethylacetate (3×100 ml)
  4. dry with materialthe combined organic phases was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-ed66918241ec4e71bcadf6a6dd908a17
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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