Potassium Carbonate → HCID 59452678, compound

HRID 419439Notes

Reaction equation

HRID 419439 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].C([O-])([O-])=O.[K+].[K+].[OH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CS(C)=O>[N+:12]([C:6]1[CH:7]=[CH:8][C:9]([N:27]2[CH2:28][CH2:29][CH:24]([OH:23])[CH2:25][CH2:26]2)=[CH:10][C:5]=1[O:4][CH2:3][C:2]([F:16])([F:15])[F:1])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 54370116HCID 54370116, compound

Product 1

HCID 59452678HCID 59452678, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Fluoro-2-nitrophenyl 2,2,2-trifluoroethyl ether (1.48 g, 6.19 mmol) was dissolved in 30 mL of DMSO with K2CO3 (1.11 g, 8.03 mmol) and 4-hydroxypiperidine (0.657 g, 6.50 mmol). The reaction was stirred for 2.5 days and quenched with H2O. The mixture was poured into EtOAc and H2O. The layers were separated, and the organic layer was washed with H2O (2×) and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 1.83 g (92%) of the title compound of step B. 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.5 Hz, 1H), 6.63 (dd, J=9.5, 2.4 Hz, 1H), 6.55 (d, J=2.4 Hz, 1H), 4.88 (q, J=8.8 Hz, 2H), 4.72 (d, J=4.2 Hz, 1H), 3.65-3.84 (m, 3H), 3.16 (ddd, J=13.3, 9.8, 2.9 Hz, 2H), 1.74 (br. s., 2H), 1.28-1.43 (m, 2H).

Workup

  1. customquenched with H2O
  2. additionThe mixture was poured into EtOAc and H2O
  3. customThe layers were separated
  4. washthe organic layer was washed with H2O (2×) and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ab59c6d89d484f8c99dd03c974002163
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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