Water → 4-Phenyl-4-(4-trifluoromethylphenoxy)piperidine

HRID 2285917Notes

Reaction equation

HRID 2285917 reaction equation
[C:1]1([C:7]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.O>CS(C)=O>[C:1]1([C:7]2([O:13][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 212682524-Phenyl-4-(4-trifluoromethylphenoxy)piperidineYield 11.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 4-phenyl-4-piperidinol (7.1 g, 40 mM), DMSO (50 ml) and sodium hydride (2 g of a 50% dispersion in oil) was heated at 80° until homogenous, cooled to ambient temperature and treated with 4-fluorobenzotrifluoride (6.6 g, 40 mM) in DMSO (10 ml). After 24 hours the reaction mixture was poured on to cold water (250 ml) and extracted with ether (2×250 ml). The combined organic layers were washed with brine, dried and the solvent removed under reduced pressure. The residue was triturated with cyclohexane, filtered and the mother liquors evaporated and the residue triturated with pentane. Sublimation of the resulting crystals at 0.1 mm Hg (bath temp. 100°) gave the title compound (1.5 g), m.p. 104°-5°.

Workup

  1. temperaturewas heated at 80° until homogenous,
  2. extractionextracted with ether (2×250 ml)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. customThe residue was triturated with cyclohexane
  7. filtrationfiltered
  8. customthe mother liquors evaporated
  9. customthe residue triturated with pentane

Sources & evidence

ORD record
ord-cd1fba3788f64c05976b042466f52790
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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