Benzyl Bromide → 4-Phenoxypiperidine

HRID 1955176Notes

Reaction equation

HRID 1955176 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)C1C=CC=CC=1>CC(C)=O>[O:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2496514-Phenoxypyridine

Product 1

HCID 188784-Phenoxypiperidine

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. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in methanol
  3. temperaturecooled to -20° C.
  4. additiontreated portionwise with sodium borohydride
  5. temperaturewarmed to 0° C
  6. customAfter a standard workup and purification
  7. dissolutionthe resulting tetrahydropyridine adduct was dissolved in methanol

Sources & evidence

ORD record
ord-93a986d1e8eb4eeeba9c468c8048196e
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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