Sodium Hydroxide → HCID 57453799, compound

HRID 2358116Notes

Reaction equation

HRID 2358116 reaction equation
[F:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1(O)[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]1.[OH-].[Na+]>>[F:1][C:2]1[C:7]([O:8][C:9]([F:10])([F:11])[F:12])=[CH:6][CH:5]=[CH:4][C:3]=1[C:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH:14]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 11659769HCID 11659769, compound

Product 1

HCID 57453799HCID 57453799, compoundYield 78.6%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[2-fluoro-3-(trifluoromethoxy)phenyl]-1-propyl-piperidin-4-ol (0.83 g, 2.6 mmol) and polyphosphoric acid (10 ml) was heated at 100° C. for 2 h. The mixture was poured on to ice and was basified with 5 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 to give the title compound (0.62 g). MS m/z (rel. intensity, 70 eV) 303 (M+, 24), 275 (14), 274 (bp), 147 (7), 133 (6).

Workup

  1. additionThe mixture was poured on to ice
  2. extractionThe mixture was extracted with ethylacetate (3×100 ml)
  3. dry with materialthe combined organic phases was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-97e7be4e10e946ceba03ad8ee754d214
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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