Potassium Carbonate → HCID 67283883, compound

HRID 1890393Notes

Reaction equation

HRID 1890393 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(C)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C.ClCCl.FC(F)(F)C(O)=O>[Cl-:15].[F:23][C:22]([F:25])([F:24])[C:19]1[CH:20]=[CH:21][C:16]([N:11]2[CH2:10][CH2:9][CH:8]([NH3+:7])[CH2:13][CH2:12]2)=[N:17][CH:18]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 67283883HCID 67283883, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

Piperidin-4-yl-carbamic acid tert-butyl ester (3.0 mmol), 2-chloro-5-trifluoromethyl-pyridine (3.0 mmol) and potassium carbonate (8.0 mmol) are dissolved in dimethylsulfoxide (10 mL), and the resulting mixture is stirred at 100° C. for 7 hours. After cooling to room temperature, the mixture is diluted with diethyl ether (30 mL), the precipitate removed by filtration and the filtrate is washed with aqueous saturated sodium hydrogencarbonate solution (2×10 mL). The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue obtained is dissolved in a 1 to 1 mixture of dichloromethane and trifluoroacetic acid (4 mL) and the reaction mixture is stirred for 1 hour at room temperature. The reaction is then concentrated under reduced pressure, the residue obtained is triturated with a 4N solution of hydrogen hydrochloride in dioxane (5 mL). The suspension is concentrated under reduced pressure and the residue obtained is triturated with diethylether. The solid obtained is filtered and dried reduced pressure to afford the desired product (62% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe precipitate removed by filtration
  3. washthe filtrate is washed with aqueous saturated sodium hydrogencarbonate solution (2×10 mL)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. stirringthe reaction mixture is stirred for 1 hour at room temperature
  9. concentrationThe reaction is then concentrated under reduced pressure
  10. customthe residue obtained
  11. customis triturated with a 4N solution of hydrogen hydrochloride in dioxane (5 mL)
  12. concentrationThe suspension is concentrated under reduced pressure
  13. customthe residue obtained
  14. customis triturated with diethylether
  15. customThe solid obtained
  16. filtrationis filtered
  17. customdried reduced pressure

Sources & evidence

ORD record
ord-d5e8e1dbad9a4ebab727a323ad611590
Source dataset
uspto-grants-2013_08
Patent number
US08507474B2

Reaction notes

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