Triethylamine → 1-(3-Fluorobenzoyl)pyrazolidin-3-one

HRID 1629972Notes

Reaction equation

HRID 1629972 reaction equation
[NH:1]1[CH2:5][CH2:4][C:3](=[O:6])[NH:2]1.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([N:1]1[CH2:5][CH2:4][C:3](=[O:6])[NH:2]1)=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99683-Fluorobenzoic AcidHCID 111923Propylphosphonic anhydrideHCID 1514973-Pyrazolidone

Product 1

HCID 711848671-(3-Fluorobenzoyl)pyrazolidin-3-oneYield 32,422.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pyrazolidin-3-one (6.9 gm, 0.080 mmol, 1 equiv.) in dry dichloromethane (70 ml), 3-fluorobenzoic acid (12.3 gm, 0.088 mmol, 1.1 equiv.), triethylamine (24.3 gm, 0.240 mmol, 3 equiv.) and 1-propane phosphonic acid cyclic anhydride (60% by weight in ethyl acetate) (51 gm, 0.16 mmol, 2 equiv.) were added in cooling condition and stirred for overnight at room temperature. The reaction mixture was concentrated and the residue was poured in water (500 ml), extracted with dichloromethane (100 ml×2) and concentrated. The crude product was purified by silica gel column using (60-120) mesh to get the pure product as yellow oil (5.4 gm, 32% yield).

Workup

  1. temperaturein cooling condition
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was poured in water (500 ml)
  4. extractionextracted with dichloromethane (100 ml×2)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-3e10c8ac1cd74efbaed5448a27f5b0dc
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

Loading…