Potassium Carbonate → 4-chloro-1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl)-1H-pyrazole

HRID 1977251Notes

Reaction equation

HRID 1977251 reaction equation
[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][N+:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3]1.[Cl:18][C:19]1[CH:20]=[N:21][NH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)C>[Cl:18][C:19]1[CH:20]=[N:21][N:22]([CH2:6][CH2:7][CH2:8][CH2:9][N:5]2[CH2:4][CH2:3][C:2]([OH:1])([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:11][CH2:10]2)[CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 275241H-Pyrazole, 4-chloro-HCID 158374988-Hydroxy-8-phenyl-5-azoniaspiro[4,5]decane

Product 1

HCID 98406224-chloro-1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl)-1H-pyrazoleYield 77.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.0 g (48 mmol) of 8-hydroxy-8-phenyl-5-azoniaspiro[4,5]decane, 5.4 g (53 mmol) of 4-chloropyrazole and 13.2 g of potassium carbonate in 200 ml of dimethylformamide is heated at reflux for 20 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform and washing is carried out repeatedly with water. The organic phase is dried with anhydrous sodium sulfate and evaporation is carried out at reduced pressure, a crude product being obtained which is suspended in ethyl ether, which is filtered while cold and which is washed with ethyl ether. 12.4 g (37.1 mmol) of 4-chloro-1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl)-1H-pyrazole are obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hours
  3. customEvaporation to dryness
  4. dissolutionthe residue is redissolved in chloroform
  5. washwashing
  6. dry with materialThe organic phase is dried with anhydrous sodium sulfate and evaporation
  7. customa crude product being obtained which
  8. filtrationwhich is filtered while cold and which
  9. washis washed with ethyl ether

Sources & evidence

ORD record
ord-67ba0e4458bf4cf0bef79ebf86abe078
Source dataset
uspto-grants-2001_05
Patent number
US06232329B1

Reaction notes

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