2-Fluoropyridine → HCID 20542602, compound

HRID 2285913Notes

Reaction equation

HRID 2285913 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][CH:20]=[CH:19][N:18]=1>CS(C)=O>[C:1]1([C:7]2([O:13][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N: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

5

Reactant 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 20542602HCID 20542602, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4-phenyl-4-piperidinol (7.1 g, 40 mM) in dry DMSO (50 ml) was treated with a 50% sodium hydride dispersion (2.0 g, 40 mM) and the mixture warmed to 80°, until a clear solution was obtained. The solution was cooled to room temperature and treated with a solution of 2-fluoropyridine (3.9 g, 40 mM) in DMSO (10 ml). After 24 hours the reaction mixture was poured onto water (250 ml) and extracted with toluene (3×250 ml). After washing with brine, the organic phase was dried (MgSO4) and the solvents removed under reduced pressure. Recrystallisation from IPE gave the title compound (3.5 g) contaminated with traces of 4-phenyl-4-piperidinol. Fractional crystallisation from cyclohexane gave the title compound analytically pure and chromatographically homogenous (600 mg) m.p. 86°-7°.

Workup

  1. temperaturethe mixture warmed to 80°, until a clear solution
  2. customwas obtained
  3. additionAfter 24 hours the reaction mixture was poured onto water (250 ml)
  4. extractionextracted with toluene (3×250 ml)
  5. washAfter washing with brine
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvents removed under reduced pressure
  8. customRecrystallisation from IPE

Sources & evidence

ORD record
ord-ebdb78e9e2544dd097157fe0bff95f66
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

Loading…