Potassium Iodide → HCID 14422883, compound

HRID 1639093Notes

Reaction equation

HRID 1639093 reaction equation
Cl[CH2:2][CH2:3][CH:4]([OH:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[F:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]([OH:14])[CH2:3][CH2:2][N:24]2[CH2:25][CH2:26][N:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)[CH2:22][CH2:23]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 14422830HCID 14422830, compound

Product 1

HCID 14422883HCID 14422883, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 9.0 g (0.0413 mole) of 4-chloro-(4-fluorophenoxy)-2-butanol, 6.8 g (0.0414 mole) of 1-(2-pyridinyl)piperazine, 14.5 g (0.1374 mole) of anhydrous sodium carbonate and 0.24 g of potassium iodide in 200 ml of 1-butanol was heated at reflux for 20 hr. The mixture was concentrated under reduced pressure and the residue was partitioned between 200 ml of water and 200 ml of benzene. The benzene layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give a thick yellow oil. Upon trituration with petroleum ether (30°-60° C.), the oil solidified. The collected solid was recrystallized from ligroin to yield 8.2 g (57%) of white, crystalline solid, m.p. 72°-73° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was partitioned between 200 ml of water and 200 ml of benzene
  5. washThe benzene layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a thick yellow oil
  9. customThe collected solid was recrystallized from ligroin
  10. customto yield 8.2 g (57%) of white, crystalline solid, m.p. 72°-73° C.

Sources & evidence

ORD record
ord-da14e6392cf8463a922aacbfed85665f
Source dataset
uspto-grants-1989_11
Patent number
US04882330

Reaction notes

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