Potassium Iodide → HCID 22715165, compound

HRID 352118Notes

Reaction equation

HRID 352118 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13]Cl.[OH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[I-].[K+].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>CN1CCCC1.O>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13][N:25]1[CH2:26][CH2:27][CH:22]([OH:21])[CH2:23][CH2:24]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 79341Piperidin-4-olHCID 444972Fumaric AcidHCID 22715106HCID 22715106, compound

Product 1

HCID 22715165HCID 22715165, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolvent

Procedure

A solution of the product from Example 22 step (b) (0.20 g, 0.61 mmol), 4-hydroxypiperidine (0.185 g, 1.83 mmol) and potassium iodide (0.051 g, 0.31 mmol) in N-methylpyrrolidine was heated to 100° C. in a sealed vessel and stirred for 4 h. The reaction was cooled, poured into water (50 ml) and the mixture extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (3×30 ml), dried (magnesium sulphate) and evaporated. The residue was dissolved in methanol and treated with one equivalent of fumaric acid. This was stirred for ten minutes then the solvent was removed in vacuo. The solid residue was triturated with ethyl acetate and the white solid obtained filtered off and dried to give the title compound (0.140 g, 45%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  3. washThe combined organic extracts were washed with water (3×30 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. dissolutionThe residue was dissolved in methanol
  7. stirringThis was stirred for ten minutes
  8. customthe solvent was removed in vacuo
  9. customThe solid residue was triturated with ethyl acetate
  10. customthe white solid obtained
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-ca17ab5854b54e72b268fcf3e668da53
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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