Hydrochloric Acid → HCID 17906331, compound

HRID 852104Notes

Reaction equation

HRID 852104 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:28]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=3[O:26][N:25]=2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[ClH:42]>O.C(Cl)(Cl)Cl.CCOCC.C(#N)C>[ClH:42].[F:33][C:31]1[CH:30]=[CH:29][C:28]2[C:24]([C:21]3[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][N:11]4[CH2:10][CH2:9][CH:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)[CH2:13][CH2:12]4)=[CH:23][CH:22]=3)=[N:25][O:26][C:27]=2[CH:32]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27591364-(4-Fluorophenyl)piperidineHCID 17906318HCID 17906318, compound

Product 1

HCID 17906331HCID 17906331, compoundYield 48%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Add 4-(4-fluoro-phenyl)-piperidine (133 mg, 0.744 mol) (See Table No.1, SM 2) to a suspension of 3-[4-(2-bromo-ethoxy)-phenyl]-6-fluoro-benzo[d]isoxazole (250 mg, 0.744 mol) in a mixture of water:acetonitrile (0.1 mL:2.5 mL). Then add potassium carbonate (164 mg, 1.63 mmol) and potassium iodide (12 mg, 1.07 mmol) and heat at reflux for 8 hours. Stir at room temperature for 72 hours, filter the suspension and wash the solid thoroughly with dichloromethane. Dilute the resulting solution with dichloromethane (5 mL) and wash with water (5 mL), 10% HCl (5 mL), water (5 mL), saturated sodium chloride (5 mL), dry (MgSO4), filter and evaporate to give a white solid. Dissolve the solid in a minimum amount of chloroform and add 1.0 M HCl in ether and stir under a nitrogen atmosphere for 1 hour. Collect the solid by vacuum filtration, wash thoroughly with ether and dry to give the title compound (168 mg, 48% Yield). Microanalysis (C, H, N) is consistent with the final, desired compound. mp-235-239° C.

Workup

  1. temperatureat reflux for 8 hours
  2. filtrationfilter the suspension
  3. washwash the solid thoroughly with dichloromethane
  4. additionDilute the resulting solution with dichloromethane (5 mL)
  5. washwash with water (5 mL), 10% HCl (5 mL), water (5 mL), saturated sodium chloride (5 mL)
  6. dry with materialdry (MgSO4)
  7. filtrationfilter
  8. customevaporate
  9. customto give a white solid
  10. stirringstir under a nitrogen atmosphere for 1 hour
  11. customCollect the solid
  12. filtrationby vacuum filtration
  13. washwash thoroughly with ether
  14. customdry

Sources & evidence

ORD record
ord-9dcd964128d34be3abefa55e5793302d
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

Loading…