Hydrogen iodide → HCID 15020365, compound

HRID 1709858Notes

Reaction equation

HRID 1709858 reaction equation
[CH:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.[P]>C(O)(=O)C>[CH:1]1([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 5462309PhosphorusHCID 15020364HCID 15020364, compound

Product 1

HCID 15020365HCID 15020365, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the free base of α-cyclohexyl-α-(4-fluorophenyl) -4-pyridinemethanol (16.54 g, 0.058 mole), 57% hydrogen iodide (250 ml), glacial acetic acid (250 ml), and phosphorus (50.0 g) was heated overnight at reflux. The reaction mixture was cooled and filtered with Celite®. The volume of the filtrate was concentrated to 100 ml. Ice/50% sodium hydroxide was added and the aqueous phase was extracted with chloroform. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give a green oil. A 4 g portion of this oil was subjected to flask chromatography on silica gel using 20% ethyl acetate-hexanes for elution. Fractions of similar purity were combined and solvent removed to give an oil. This oil was dried in vacuo overnight at 80° C. The oil crystallized to give 2.95 g (33.9% yield) of white, crystalline solid, m.p. 78°-81° C.

Workup

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered with Celite®
  5. concentrationThe volume of the filtrate was concentrated to 100 ml
  6. additionIce/50% sodium hydroxide was added
  7. extractionthe aqueous phase was extracted with chloroform
  8. dry with materialThe chloroform layer was dried over sodium sulfate
  9. filtrationfiltered
  10. customsolvent removed
  11. customto give a green oil
  12. customA 4 g portion of this oil was subjected to flask
  13. washchromatography on silica gel using 20% ethyl acetate-hexanes for elution
  14. customsolvent removed
  15. customto give an oil
  16. customThis oil was dried in vacuo overnight at 80° C
  17. customThe oil crystallized
  18. customto give 2.95 g (33.9% yield) of white, crystalline solid, m.p. 78°-81° C.

Sources & evidence

ORD record
ord-778cf4e9069146598c1cfe1e2a066ddf
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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