Potassium Iodide → HCID 20500939, compound

HRID 851696Notes

Reaction equation

HRID 851696 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:12].[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][N:29]3[C:33]([CH2:34][CH3:35])=[N:32][NH:31][C:30]3=[O:36])[CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[OH2:1].[ClH:13].[ClH:12].[Cl:13][C:14]1[CH:15]=[C:16]([N:20]2[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][CH2:28][N:29]3[C:33]([CH2:34][CH3:35])=[N:32][N:31]([CH2:10][CH2:9][CH2:8][O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:30]3=[O:36])[CH2:24][CH2:25]2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 20500938HCID 20500938, compound

Product 1

HCID 20500939HCID 20500939, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-phenoxypropyl bromide (3.01 g., 0.014 mole), 4-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride (5.4 g., 0.014 mole), pulverized potassium carbonate (5.8 g., 0.042 mole) and a trace of potassium iodide in 50 ml. of acetonitrile is refluxed for a 20 hr. period. The hot reaction mixture is filtered, the filtrate concentrated under reduced pressure and residual material taken up in chloroform and filtered. Solvent is removed and further purification carried out chromatographically employing a silica gel column with ethanol/chloroform eluent. The chromatographically purified material is taken up in ether and acidified with ethanolic hydrogen chloride to provide a solid which is triturated with ethanol to provide 1.6 g. (20% yield) of 4-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-2-(3-phenoxypropyl)-3H-1,2,4-triazol-3-one dihydrochloride hydrate, m.p. 146°-148° C.

Workup

  1. filtrationThe hot reaction mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure and residual material
  3. filtrationfiltered
  4. customSolvent is removed
  5. customfurther purification
  6. customto provide a solid which
  7. customis triturated with ethanol
  8. customto provide 1.6 g

Sources & evidence

ORD record
ord-e309e1057ed94f7dae0e0fbeb6d0625d
Source dataset
uspto-grants-1983_05
Patent number
US04386091

Reaction notes

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