Potassium Iodide → HCID 70573063, compound

HRID 2286357Notes

Reaction equation

HRID 2286357 reaction equation
[CH2:1]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC1C=CC(C(C(Cl)C[O:33][CH2:34][CH:35](Cl)[CH:36]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)C2C=CC(F)=CC=2)=CC=1.[C:53](=[O:56])([O-:55])[O-].[K+].[K+].[I-].[K+].[CH2:61]([C:65](C)=[O:66])C(C)C>>[C:34]([OH:66])(=[O:33])/[CH:35]=[CH:36]\[C:53]([OH:55])=[O:56].[F:50][C:47]1[CH:46]=[CH:45][C:44]([CH:36]([C:37]2[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=2)[O:66][CH2:65][CH2:61][N:13]2[CH2:14][CH2:15][N:10]([CH2:1][CH:2]=[CH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:11][CH2:12]2)=[CH:49][CH:48]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 7909Methyl Isobutyl KetoneHCID 11430Potassium CarbonateHCID 86803CinnamylpiperazineHCID 57133902HCID 57133902, compound

Product 1

HCID 70573063HCID 70573063, compound

Procedure

A mixture of 10.45 g (0.052 mole) of 1-cinnamylpiperazine, 29.2 g (0.104 mole) of bis(p-fluorophenyl)methyl-2-chloroethyl ether, 12.5 g (0.09 mole) of potassium carbonate, 2 g (0.012 mole) of potassium iodide and 250 ml of methyl isobutyl ketone was refluxed for 24 hours. The precipitate was filtered off and the filtrate was concentrated by evaporation of the solvent. Water and diethyl ether were added to the residue, the ethereal phase was separated off and dried over sodium sulphate. Then an ethereal maleic acid solution was added until the reaction mixture was acidic. The resulting precipitate was filtered off and recrystallized from a mixture of isopropyl alcohol and diethyl ether. 1-{2-[Bis(p-fluorophenyl)methoxy]ethyl}-4-(3-phenylprop-2-enyl)piperazine maleate (1:2) was obtained. It melted at 192°-194° C. The hydrochloride (1:2) melts at 211.5°-212° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated by evaporation of the solvent
  4. additionWater and diethyl ether were added to the residue
  5. customthe ethereal phase was separated off
  6. dry with materialdried over sodium sulphate
  7. additionThen an ethereal maleic acid solution was added until the reaction mixture
  8. filtrationThe resulting precipitate was filtered off
  9. customrecrystallized from a mixture of isopropyl alcohol and diethyl ether

Sources & evidence

ORD record
ord-8179e688d3c64a7ba004ff3114c6ac23
Source dataset
uspto-grants-1981_05
Patent number
US04265894

Reaction notes

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