Dimethylformamide → HCID 11470752, compound

HRID 2099011Notes

Reaction equation

HRID 2099011 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.O=P(Cl)(Cl)Cl.CN([CH:25]=[O:26])C>>[F:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:25]=[O:26])=[C:12]([OH:16])[CH:11]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 11206864HCID 11206864, compound

Product 1

HCID 11470752HCID 11470752, compound

Conditions

Temperature
0 °C

Procedure

600 mg (2.675 mmol) 3-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-phenol are dissolved in 8 mL DMF and cooled to 0° C. 0.27 mL (1.1 eq) POCl3 is added dropwise within 2 min. and the reaction mixture stirred for an additional 5 min. before being allowed to reach room temperature, and then heated and stirred for 3 h at 90° C. The reaction mixture is evaporated and the residue extracted with water and ethyl acetate. The organic phases are washed with brine, dried over sodium sulphate and evaporated. The residue is column chromatographed (silica gel, ethyl acetate followed by ethyl acetate/MeOH 85:15) to yield the desired product as a yellowish oil.

Workup

  1. customto reach room temperature
  2. temperatureheated
  3. stirringstirred for 3 h at 90° C
  4. customThe reaction mixture is evaporated
  5. extractionthe residue extracted with water and ethyl acetate
  6. washThe organic phases are washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customchromatographed (silica gel, ethyl acetate followed by ethyl acetate/MeOH 85:15)

Sources & evidence

ORD record
ord-a58f1c4563584029b7399820a0d8be5e
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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