Potassium Iodide → HCID 13078367, compound

HRID 223251Notes

Reaction equation

HRID 223251 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][N:9]=2)[CH2:4][CH2:3]1.[Cl:17][CH2:18][CH2:19][CH2:20][CH:21]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(OCC)C.O.CN(C)C=O>[ClH:17].[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH:21]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH2:20][CH2:19][CH2:18][N:2]2[CH2:3][CH2:4][CH:5]([C:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[O:10][N:9]=3)[CH2:6][CH2:7]2)=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 130764373-(4-Piperidinyl)-1,2-benzisoxazole Hydrochloride

Product 1

HCID 13078367HCID 13078367, compoundYield 29.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.94 g of 3-(4-piperidyl)-1,2-benzisoxazole hydrochloride, 4.60 g of 4-chloro-1,1-bis(4-fluorophenyl)butane, 4.95 g of anhydrous potassium carbonate, a few crystals of potassium iodide and 85 ml of dimethylformamide were stirred and heated at 90° for 8 hrs and then stirred at ambient temperature over the weekend. The mixture was poured into water and extracted with ethyl acetate and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was dissolved in anhydrous diethyl ether and a sautrated hydrogen chloride-ether solution was added dropwise to precipitate a gum. The gum was recrystallized from ethyl acetate-ether to yield a solid. The mother liquor was concentrated to yield an additional solid. The solids were combined and recrystallized twice from ethyl acetate-ether to yield 2.35 g (29.5%) of product, mp, 156°-157°.

Workup

  1. temperatureheated at 90° for 8 hrs
  2. extractionextracted with ethyl acetate and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto yield an oil
  6. customto precipitate a gum
  7. customThe gum was recrystallized from ethyl acetate-ether
  8. customto yield a solid
  9. concentrationThe mother liquor was concentrated
  10. customto yield an additional solid
  11. customrecrystallized twice from ethyl acetate-ether

Sources & evidence

ORD record
ord-8ce51170782548f1b8fe581d7fb1cbf8
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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