Potassium Iodide → HCID 20245072, compound

HRID 1153961Notes

Reaction equation

HRID 1153961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21](=[O:22])[N:20]=[C:19]([CH2:23][CH3:24])[NH:18]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:25]([CH2:32][CH2:33][CH2:34][CH2:35]Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21](=[O:22])[N:20]([CH2:35][CH2:34][CH2:33][CH2:32][O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:19]([CH2:23][CH3:24])=[N:18]3)[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 70986(4-Bromobutoxy)benzeneHCID 178437794HCID 178437794, compound

Product 1

HCID 20245072HCID 20245072, compound

Reagents, catalysts & solvents 1

HCID 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), 4-phenoxybutyl bromide (2.29 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. Concentration of ethereal filtrate affords the free base. Conversion of the free base to the hydrochloride salt in ethanol with ethanolic hydrogen chloride and crystallization of the salt from ethanol affords analytically pure 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(4-phenoxybutyl)-3H-1,2,4-triazol-3-one hydrochloride, m.p. 152°-154° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate concentrated under reduced pressure and residual material
  3. filtrationfiltered
  4. customConcentration of ethereal filtrate affords the free base
  5. customConversion of the free base to the hydrochloride salt in ethanol with ethanolic hydrogen chloride and crystallization of the salt from ethanol

Sources & evidence

ORD record
ord-12f902dc0689451ca3dc0bb1f0cd74d8
Source dataset
uspto-grants-1984_12
Patent number
US04487773

Reaction notes

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