Azide → HCID 22605624, compound

HRID 2307434Notes

Reaction equation

HRID 2307434 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[N-:17]=[N+:18]=[N-:19].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:17]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:4]=1)[CH3:9])=[N+:18]=[N-:19]

Participants

6

Reactant 3

HCID 33558AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22605547HCID 22605547, compound

Product 1

HCID 22605624HCID 22605624, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-fluoro-3-morpholin-4-yl-phenyl)ethanol (3.7 g) and diphenylphosphory azide (6.765) in toluene (24 mL) at 0° C. was added a solution of DBU (3.74 g) in toluene (2 mL) and the resulting solution was stirred at 0° C. for 2 hours. The reaction mixture was warmed to room temperature and then stirred for 16 hours. The reaction was diluted with ethyl acetate and quenched with water. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (10% ethyl acetate in hexane) to give 3.71 g of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 16 hours
  3. customquenched with water
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0f679c4edec24e8995dd9eb5c35c598f
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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