Hydrochloric Acid → HCID 20500937, compound

HRID 851695Notes

Reaction equation

HRID 851695 reaction equation
Cl.[Cl:2]C1C=C(N2CCN(CCCN3C(CC)=NNC3=O)CC2)C=CC=1.O(CCBr)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:44][C:45]1[CH:46]=[C:47]([N:51]2[CH2:56][CH2:55][N:54]([CH2:57][CH2:58][CH2:59][N:60]3[C:64]([CH2:65][CH3:66])=[N:63][N:62]([CH2:67][CH2:68][O:69][C:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)[C:61]3=[O:76])[CH2:53][CH2:52]2)[CH:48]=[CH:49][CH:50]=1.Cl>C(O)C.C(#N)C>[ClH:2].[Cl:44][C:45]1[CH:46]=[C:47]([N:51]2[CH2:52][CH2:53][N:54]([CH2:57][CH2:58][CH2:59][N:60]3[C:64]([CH2:65][CH3:66])=[N:63][N:62]([CH2:67][CH2:68][O:69][C:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)[C:61]3=[O:76])[CH2:55][CH2:56]2)[CH:48]=[CH:49][CH:50]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 13151055HCID 13151055, compoundHCID 20500938HCID 20500938, compound

Product 1

HCID 20500937HCID 20500937, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride (10.8 g., 0.028 mole), phenoxyethyl bromide (5.83 g., 0.028 mole), potassium carbonate (11.6 g., 0.084 mole) and a trace of potassium iodide in 100 ml. of acetonitrile is refluxed for a 66 hr. period. The hot reaction mixture is filtered, the filtrate concentrated under reduced pressure and residual material taken up in chloroform. The chloroform solution is washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to provide 13.2 g. of the free base product, 4-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-2-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one. The free base is converted to the hydrochloride salt in ethanol with ethanolic hydrogen chloride and crystallized from ethanol to afford a 71% yield of analytically pure 4-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-2-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride, m.p. 175°-177° C.

Workup

  1. filtrationThe hot reaction mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure and residual material
  3. washThe chloroform solution is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide 13.2 g
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-b0d26b39a506458fbf5bd2b87e37cedd
Source dataset
uspto-grants-1983_05
Patent number
US04386091

Reaction notes

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