1-Phenylpiperidine → HCID 10064740, compound

HRID 2248569Notes

Reaction equation

HRID 2248569 reaction equation
[S:1](=[O:4])(=O)=[O:2].[O:5]1[CH2:10][CH2:9]OCC1.[C:11]1([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[N:17]1([C:11]2[CH:16]=[CH:15][C:14]([S:1]([N:17]3[CH2:11][CH2:12][CH2:13][CH2:9][C:10]3=[O:5])(=[O:4])=[O:2])=[CH:13][CH:12]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 200381-PhenylpiperidineHCID 24682Sulfur trioxideHCID 312751,4-Dioxane

Product 1

HCID 10064740HCID 10064740, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution, cooled to between 0° C. and -5° C., comprising 8.46 g of sulphur trioxide in 45 cm3 of methylene chloride, there are added dropwise 9.3 g of dioxane followed by 17.1 g of N-phenylpiperidine dissolved in 45 cm3 of methylene chloride. The mixture is allowed to return to room temperature, then heated to reflux for 1 hour and evaporated to dryness, the residue is neutralized with 10% strength sodium carbonate solution, the aqueous phase is concentrated and the residue is dried and treated with 200 cm3 of phosphoryl chloride and 21.8 g of phosphorus pentachloride for 12 hours at room temperature. The mixture is evaporated to dryness, the residue is taken up in chloroform with a little water, the organic phase is separated, dried over sodium sulphate and filtered and the solvent is evaporated off. 19 g of expected product are obtained, which product is used as it is in the next stage.

Workup

  1. temperatureTo a solution, cooled to between 0° C. and -5° C.
  2. customto return to room temperature
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. customevaporated to dryness
  6. concentrationthe aqueous phase is concentrated
  7. customthe residue is dried
  8. additiontreated with 200 cm3 of phosphoryl chloride and 21.8 g of phosphorus pentachloride for 12 hours at room temperature
  9. customThe mixture is evaporated to dryness
  10. customthe organic phase is separated
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-b2d613a171d3434b8b1f570f4c1fc72f
Source dataset
uspto-grants-1991_08
Patent number
US05041436

Reaction notes

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