Potassium Carbonate → HCID 15895338, compound

HRID 1955177Notes

Reaction equation

HRID 1955177 reaction equation
[O:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 188784-PhenoxypiperidineHCID 2600041-(3-Bromopropoxy)-4-fluorobenzene

Product 1

HCID 15895338HCID 15895338, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-phenoxypyridine and benzylbromide in acetone was stirred overnight at room temperature. After removal of the solvent, the residue was dissolved in methanol, cooled to -20° C. and treated portionwise with sodium borohydride, and warmed to 0° C. After a standard workup and purification, the resulting tetrahydropyridine adduct was dissolved in methanol and hydrogenated using 20% Pd-C as a catalyst to provide 4-phenoxypiperidine. A mixture of 4-phenoxypiperidine and 1-bromo-3-(4-fluorophenoxy)propane in acetone with excess potassium carbonate was heated at reflux for 12 hours to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours

Sources & evidence

ORD record
ord-31ad0bdc912a49ec9a5f4fb96d7d83c5
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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