Water → 2-(1-Methyl-4-phenyl-4-piperidinyloxy)pyridine

HRID 2285906Notes

Reaction equation

HRID 2285906 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([O:8][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 205426042-(1-Methyl-4-phenyl-4-piperidinyloxy)pyridineYield 37.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-methyl-4-phenyl-4-piperidinol (prepared by reaction of 1-methyl-4-piperidone with phenyl lithium; 3.83 g, 20 mM) in dry DMSO (50 ml) was treated with sodium hydride (960 mg of 50% dispersion in oil, 20 mM), stirred for 1 hour then treated with 2-fluoro-pyridine (1.94 g, 20 mM). After 48 hours the reaction was poured on to water (200 ml) and extracted with ether (3×200 ml). The organic extract was washed with brine, dried and the solvent removed under reduced pressure. Recrystallisation of the residue from cyclohexane gave the title compound (2.0 g,) m.p. 95°-6° C.

Workup

  1. extractionextracted with ether (3×200 ml)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. customRecrystallisation of the residue from cyclohexane

Sources & evidence

ORD record
ord-e770744589ae4a429c0b658ee622cc96
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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