1-Phenylpiperazine → HCID 19079292, compound

HRID 53175Notes

Reaction equation

HRID 53175 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([CH2:11][CH2:12]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=[C:5]2[O:4][C:3]1=[O:24].[C:25]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>O1CCOCC1>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([CH2:11][CH2:12][N:34]3[CH2:35][CH2:36][N:31]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:32][CH2:33]3)[CH:10]=[C:5]2[O:4][C:3]1=[O:24]

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 19079297HCID 19079297, compound

Product 1

HCID 19079292HCID 19079292, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-methyl-6-[2-(p-toluenesulfonyloxy)ethyl]oxazolo[4,5-b]pyridin-2(3H)-one of Preparation 15 (210 mg, 1.2 mmol) is dissolved in 1,4-dioxane (8 ml). N-phenylpiperazine (0.10 ml, 1.38 mmol) and triethylamine (0.18 ml, 1.3 mmol) are added in succession to the reaction mixture. Stirring is maintained at room temperature for 24 hours. After the solvent has been evaporated off under reduced pressure, the residue is taken up in water. Extraction is carried out with dichloromethane and the organic phase is dried over magnesium sulfate and filtered, and then the solvent is evaporated off. The title product is purified by chromatography on silica gel (eluant: dichloromethane/methanol: 95/5). The yield obtained is 91%. ##STR66##

Workup

  1. customAfter the solvent has been evaporated off under reduced pressure
  2. extractionExtraction
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off
  6. customThe title product is purified by chromatography on silica gel (eluant: dichloromethane/methanol: 95/5)
  7. customThe yield obtained

Sources & evidence

ORD record
ord-2ce83ce816f1445cbdf66e3404b8f6a1
Source dataset
uspto-grants-1997_04
Patent number
US05618819

Reaction notes

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