Potassium Iodide → HCID 70573063, compound

HRID 1395238Notes

Reaction equation

HRID 1395238 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 crystallized 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. customcrystallized from a mixture of isopropyl alcohol and diethyl ether

Sources & evidence

ORD record
ord-d20780fd836042b9a3db820f3f84a46c
Source dataset
uspto-grants-1980_05
Patent number
US04202896

Reaction notes

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