Water → HCID 13823209, compound

HRID 232020Notes

Reaction equation

HRID 232020 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][CH2:8][O:9][N:10]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH:12]=[N:11]1.O.S(=O)(=O)(O)O>O1CCCC1>[O:1]=[CH:2][CH2:6][CH2:7][CH2:8][O:9][N:10]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH:12]=[N:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13823208HCID 13823208, compound

Product 1

HCID 13823209HCID 13823209, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 g of 1-[3-(2-dioxolanyl)-propoxy]-4-(N-piperidinylcarbonyl)-pyrazole in a mixture of 150 ml of tetrahydrofuran, 200 ml of water and 4 ml of concentrated sulfuric acid are refluxed for 8 hours. The mixture is cooled and then saturated with sodium chloride, the phases are separated and the aqueous phase is extracted again with tetrahydrofuran. The combined organic phases are evaporated down, the residue is taken up with methylene chloride, the solution is washed with water and the solvent is evaporated off to give 33 g of the title compound in the form of a viscous oil.

Workup

  1. temperatureare refluxed for 8 hours
  2. temperatureThe mixture is cooled
  3. customsaturated with sodium chloride, the phases are separated
  4. extractionthe aqueous phase is extracted again with tetrahydrofuran
  5. customThe combined organic phases are evaporated down
  6. washthe solution is washed with water
  7. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-66511f60a3c040a58a09ed1ecb638d84
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

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