Potassium Iodide → HCID 13369910, compound

HRID 1153960Notes

Reaction equation

HRID 1153960 reaction equation
ClC1C=C(N2CCN(CCCN3C(=O)N=C(CC)N3)CC2)C=CC=1.O(CCCBr)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl.[Cl:45][C:46]1[CH:47]=[C:48]([N:52]2[CH2:57][CH2:56][N:55]([CH2:58][CH2:59][CH2:60][N:61]3[C:65](=[O:66])[N:64]([CH2:67][CH2:68][CH2:69][O:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)[C:63]([CH2:77][CH3:78])=[N:62]3)[CH2:54][CH2:53]2)[CH:49]=[CH:50][CH:51]=1>C(O)C.C(#N)C>[Cl:45][C:46]1[CH:47]=[C:48]([N:52]2[CH2:53][CH2:54][N:55]([CH2:58][CH2:59][CH2:60][N:61]3[C:65](=[O:66])[N:64]([CH2:67][CH2:68][CH2:69][O:70][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=4)[C:63]([CH2:77][CH3:78])=[N:62]3)[CH2:56][CH2:57]2)[CH:49]=[CH:50][CH:51]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 20435662HCID 20435662, compoundHCID 178437794HCID 178437794, compound

Product 1

HCID 13369910HCID 13369910, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-1H-1,2,4-triazol-3(2H)-one (3.86 g., 0.01 mole), 3-phenoxypropyl bromide (2.15 g., 0.01 mole), potassium carbonate (4.15 g., 0.01 mole) and a trace of potassium iodide in 50 ml. of acetonitrile is refluxed for a 65 hr. period. The reaction mixture is filtered, the filtrate concentrated under reduced pressure and residual material taken up in ether and filtered. Solvent is removed and further purification carried out by sequentially converting the free base to the hydrochloride salt and then to the free base which is chromatographically treated employing a silica column with methanol/chloroform eluant. Free base, obtained from the chromatographic separation, is converted to the hydrochloride salt in ethanol employing ethanolic hydrogen chloride to afford 1.17 g., (22% yield) of analytically pure 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(3-phenoxypropyl)-3H-1,2,4-triazol-3-one hydrochloride, m.p. 145°-147° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure and residual material
  3. filtrationfiltered
  4. customSolvent is removed
  5. customfurther purification
  6. additionto the free base which is chromatographically treated
  7. customFree base, obtained from the chromatographic separation
  8. customto afford 1.17 g

Sources & evidence

ORD record
ord-7a90eb3792cb405a95f1b8538b72feda
Source dataset
uspto-grants-1984_12
Patent number
US04487773

Reaction notes

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