Potassium Phosphate, Tribasic → HCID 49760180, compound

HRID 1411403Notes

Reaction equation

HRID 1411403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([F:9])[C:7]=1F.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:21]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[F:9][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=[C:2]([F:1])[C:7]=1[N:30]1[CH2:31][CH2:32][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 698734-PhenylpiperidineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 49760180HCID 49760180, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 100 mL round-bottom flask was mixed 3,4,5-trifluoronitrobenzene (1.751 mL, 15 mmol) and potassium phosphate, dibasic (5.23 g, 30.0 mmol) in DMSO (15.00 mL) to give a yellow suspension. 4-Phenylpiperidine (2.419 g, 15.00 mmol) was added portion-wise as a solid over 10 minutes to produce a deeper yellow suspension and a mild exotherm. The mixture was stirred for 1 hour and partitioned between EtOAc and water. The EtOAc layer was washed 2× by 50 mL each with water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a yellow solid (4.53 g, 95% yield).

Workup

  1. customto give a yellow suspension
  2. customto produce a deeper yellow suspension
  3. custompartitioned between EtOAc and water
  4. washThe EtOAc layer was washed 2× by 50 mL each with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-284b9716430047efb6393ca67a42b67c
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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