Water → HCID 20542611, compound

HRID 2285908Notes

Reaction equation

HRID 2285908 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+].Cl[C:18]1[CH:23]=[N: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]=[N:22][CH:21]=[CH:20][N:19]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73277ChloropyrazineHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 20542611HCID 20542611, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 1-methyl-4-phenyl-4-piperidinol (7.65 g, 40 mM), in DMSO (100 ml) was treated with 50% sodium hydride dispersion (2.0 g, 40 mM) and the mixture warmed to 80° until a clear solution was obtained. After cooling to room temperature a solution of 2-chloropyrazine (5.6 g, 40 mM) in DMSO (10 ml) was added. After 48 hours the reaction mixture was poured on to water (400 ml), extracted with ether (3×250 ml), the organic phase dried and the solvents removed under reduced pressure. Recrystallisation of the residue from cyclohexane gave recovered 1-methyl-4-phenyl-4-piperidinol (2 g). Chromatography of the mother liquors on Grade III silica using 3% methanol in chloroform as eluant, evaporation of the appropriate fractions and recrystallisation from pentane gave the title compound (1.2 g) m.p. 115°-6° C.

Workup

  1. temperaturethe mixture warmed to 80° until a clear solution
  2. customwas obtained
  3. additionwas added
  4. extractionextracted with ether (3×250 ml)
  5. customthe organic phase dried
  6. customthe solvents removed under reduced pressure
  7. customRecrystallisation of the residue from cyclohexane
  8. customgave
  9. customrecovered 1-methyl-4-phenyl-4-piperidinol (2 g)
  10. customChromatography of the mother liquors on Grade III silica using 3% methanol in chloroform as eluant, evaporation of the appropriate fractions and recrystallisation from pentane

Sources & evidence

ORD record
ord-6546429934e441608594772aa84c2d1a
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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