Water → HCID 14837067, compound

HRID 2072815Notes

Reaction equation

HRID 2072815 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([OH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:23][C:24]1[C:29](F)=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:25]=1[F:34].O>CN(C)C=O>[CH2:3]([N:10]1[CH2:11][CH2:12][C:13]([O:22][C:29]2[C:28]([F:31])=[C:27]([F:32])[C:26]([F:33])=[C:25]([F:34])[C:24]=2[F:23])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9805HexafluorobenzeneHCID 24758Sodium hydrideHCID 973334-Piperidinol, 1-benzyl-4-phenyl-

Product 1

HCID 14837067HCID 14837067, compoundYield 14.53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% in oil, 4.0 g) in 75 ml of dimethylformamide was added a solution of 22.69 g of 1-benzyl-4-hydroxy-4-phenyl piperidine in 100 ml of dimethylformamide. The mixture was heated with a heat gun to initiate evolution of gas. When evolution had ceased, the mixture was cooled to ice bath temperature and 18.61 g of hexafluorobenzene was added, dropwise, and the reaction was allowed to proceed for 20 hours. The reaction mixture was then poured into 500 ml of iced water and the aqueous suspension extracted with ethyl acetate. The organic layer was washed with water, followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the solvent afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 10% ethyl acetate/dichloromethane) to yield 5.36 g, (14.53%) of 1-benzyl-4-(2,3,4,5,6,-pentafluorophenoxy)-4-phenyl piperidine, m.p. 80°-83° C.

Workup

  1. temperatureThe mixture was heated with a heat gun
  2. additionwas added
  3. extractionthe aqueous suspension extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customevaporation of the solvent
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-17b25838d65f4e67a84387a31bfbf77b
Source dataset
uspto-grants-1990_04
Patent number
US04914204

Reaction notes

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