Hydrochloric Acid → HCID 15390883, compound

HRID 650986Notes

Reaction equation

HRID 650986 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Cl>O1CCOCC1.C(O)C>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 15390901HCID 15390901, compound

Product 1

HCID 15390883HCID 15390883, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1.72 g of 5-[2-(2-bromoethyl)oxy-phenyl]-3-phenyl-1,2,4-oxadiazole are dissolved in 50 ml of anhydrous dioxane and mixed with 2 g of N-methylpiperazine. The solution is refluxed for one hour and then concentrated by evaporation in vacuo. The residue is chromatographed on silica gel with dichloromethane/methanol (90/10). The base thus obtained is dissolved in anhydrous ethanol, acidified with ethereal HCl and precipitated with diethyl ether. The residue is recrystallised from anhydrous ethanol and diethylether. Yield: 1.7 g (78% of theory). m.p.: 251-253° C.

Workup

  1. temperatureThe solution is refluxed for one hour
  2. concentrationconcentrated by evaporation in vacuo
  3. customThe residue is chromatographed on silica gel with dichloromethane/methanol (90/10)
  4. customThe base thus obtained
  5. customprecipitated with diethyl ether
  6. customThe residue is recrystallised from anhydrous ethanol and diethylether

Sources & evidence

ORD record
ord-01caec902cb94490acc9470fc8551e29
Source dataset
uspto-grants-2001_08
Patent number
US06277872B1

Reaction notes

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