Water → HCID 20542605, compound

HRID 2285911Notes

Reaction equation

HRID 2285911 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:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[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:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 20542605HCID 20542605, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 1-methyl-4-phenyl-4-piperidinol (7.65 g, 40 mM) in DMSO (50 ml) was treated with 50% sodium hydride dispersion (2 g, 40 mM) and warmed to 80° until a homogenous solution was obtained. After cooling to room temperature, the mixture was treated with a solution of 2-chloroquinoline (6.55 g, 40 mM) in DMSO (10 ml). After 24 hours the mixture was poured on to water (250 ml) and extracted with toluene (3×250 ml). After drying and evaporation of the solvents, the residue crystallised from cyclohexane to give recovered 1-methyl-4-phenyl-4-piperidinol (2.7 g). Chromatography of the mother liquors on Grade III silica, using 3% methanol in chloroform as eluant gave the title compound (3 g) contaminated with a small quantity of 2-quinolone which was removed by crystallisation from cyclohexane. Recrystallisation of the mother liquors from pentane gave the title compound (1.2 g) m.p. 80°-1° C.

Workup

  1. temperaturewarmed to 80° until a homogenous solution
  2. customwas obtained
  3. extractionextracted with toluene (3×250 ml)
  4. customAfter drying
  5. customevaporation of the solvents
  6. customthe residue crystallised from cyclohexane
  7. customto give
  8. customrecovered 1-methyl-4-phenyl-4-piperidinol (2.7 g)

Sources & evidence

ORD record
ord-ab721bff32934213b760fd467130e783
Source dataset
uspto-grants-1982_04
Patent number
US04325953

Reaction notes

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