Hexafluorobenzene → HCID 14649995, compound

HRID 1721860Notes

Reaction equation

HRID 1721860 reaction equation
[H-].[Na+].[C:3]([N:6]1[CH2:11][CH2:10][C:9]([OH:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[F:19][C:20]1[C:25](F)=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:21]=1[F:30]>CN(C)C=O>[C:3]([N:6]1[CH2:11][CH2:10][C:9]([O:18][C:25]2[C:24]([F:27])=[C:23]([F:28])[C:22]([F:29])=[C:21]([F:30])[C:20]=2[F:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 9805HexafluorobenzeneHCID 24758Sodium hydrideHCID 11715514HCID 11715514, compound

Product 1

HCID 14649995HCID 14649995, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A stirred suspension of sodium hydride (60% in oil, 1.6 g) in 50 ml of dimethylformamide was treated with 7.0 g of 1-acetyl-4-hydroxy-4-phenylpiperidine in 100 ml of dimethylformamide. After the evolution of gas had ceased, the mixture was cooled to ice bath temperature and a solution of 6.88 g of hexafluorobenzene in 50 ml of dimethylformamide was added, dropwise. After stirring for 20 hours at ambient temperature the mixture was poured into ice water and then extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane to yield 9.06 g (73.5%) of 1-acetyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine, m.p. 115°-120° C.

Workup

  1. temperaturethe mixture was cooled to ice bath temperature
  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
  7. customThe concentrate was purified by means of high pressure liquid chromatography (silica gel
  8. washelution with 50% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-3365a99a13824a668b98bbfd1e402c10
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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