Water → 4-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidine

HRID 1721857Notes

Reaction equation

HRID 1721857 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[F:16][C:17]1[C:22](F)=[C:21]([F:24])[C:20]([F:25])=[C:19]([F:26])[C:18]=1[F:27].O>CN(C)C=O>[F:16][C:17]1[C:18]([F:27])=[C:19]([F:26])[C:20]([F:25])=[C:21]([F:24])[C:22]=1[O:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 9805HexafluorobenzeneHCID 24758Sodium hydrideHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 146499784-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidineYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

A suspension of sodium hydride (60% in oil, 6.4 g) in 50 ml of dry dimethylformamide was treated with a solution of 2.5 g of 4-hydroxy-4-phenylpiperidine in 100 ml of dry dimethylformamide over a period of ten minutes. After heating at 50° C. for 30 minutes the mixture was cooled to 5° C. and a solution of 18.6 ml of hexafluorobenzene in 100 ml of dry dimethylformamide was added, dropwise, over a period of 30 minutes. The reaction mixture was then stirred at ambient temperature for 20 hours, poured into 500 ml of water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 21 g (44%) of 4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine.

Workup

  1. temperaturewas cooled to 5° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9956c2bbc664c2f82cb3e49806803ce
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

Loading…