Methanol → HCID 19088006, compound

HRID 1464425Notes

Reaction equation

HRID 1464425 reaction equation
O[CH:2]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].CCN(S(F)(F)[F:25])CC.CO>O1CCOCC1>[F:25][CH:2]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 50981PimonidazoleHCID 123472(Diethylamino)sulfur trifluoride2×

Product 1

HCID 19088006HCID 19088006, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.2 g (8.65 mmol) of 1-(2'-hydroxy-3'-piperidylpropyl)-2-nitroimidazole in 20 ml of dry dioxane, 2.5 g (15.5 mmol) of DAST was dropwise added with cooling by ice and reacted for 5 hours at room temperature. After reaction, to the solution, 10 ml of methanol was added to decompose excess DAST. Then, the solution was concentrated and partitioned between chloroform and water. The pH of the aqueous phase was adjusted to 12 by the addition of an aqueous solution of sodium hydroxide and the liquid was again partitioned between chloroform and water. The chloroform phase was dried on magnesium sulfate and filtered. The filtrate was concentrated and subjected to isolation and purification by silica gel chromatography to give 1-(2'-fluoro-3'-piperidylpropyl)-2-nitroimidazole, which was treated with hydrochloric acid to form a hydrochloride and crystallized from ethanol to give 560 mg of crystalline hydrochloride of 1-(2'-fluoro-3'-piperidylpropyl)-2-nitroimidazole.

Workup

  1. temperaturewith cooling by ice
  2. customreacted for 5 hours at room temperature
  3. customAfter reaction
  4. concentrationThen, the solution was concentrated
  5. custompartitioned between chloroform and water
  6. additionThe pH of the aqueous phase was adjusted to 12 by the addition of an aqueous solution of sodium hydroxide
  7. customthe liquid was again partitioned between chloroform and water
  8. dry with materialThe chloroform phase was dried on magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customsubjected to isolation and purification by silica gel chromatography

Sources & evidence

ORD record
ord-135d8a6e467c408c990f988bb276e74f
Source dataset
uspto-grants-1994_04
Patent number
US05304654

Reaction notes

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