Sodium Iodide → HCID 9828743, compound

HRID 1003741Notes

Reaction equation

HRID 1003741 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)=[C:10]([C:20]([O:22][CH3:23])=[O:21])[NH:9][C:8]1=[O:24].[CH3:25][O:26][C:27]([C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O1CCOCC1>[CH3:25][O:26][C:27]([C:29]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=3)=[C:10]([C:20]([O:22][CH3:23])=[O:21])[NH:9][C:8]2=[O:24])[CH2:33][CH2:34]1)=[O:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 545827Methyl 4-phenylpiperidine-4-carboxylateHCID 15462012HCID 15462012, compound

Product 1

HCID 9828743HCID 9828743, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-(5-bromopent-1-yl)-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone (0.357 g, 0.88 mmol) in dioxane (10 mL) was added 4-methoxycarbonyl-4-phenylpiperidine (0.388 g, 1.77 mmol), potassium carbonate (0.544 g, 2.65 mmol) and sodium iodide (0. g, 1.77 mmol), and the mixture refluxed for 24 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between chloroform (40 mL) and water (5 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (ethyl acetate: methanol, 4.4:0.6) to yield 0.235 g (48%) of the required product as a colorless oil. Hydrochloride salt (recrystallized from ether) : white solid; m.p. 180-182° C. Analysis calculated for C29H34ClF2N3O5.1.7 H2O: C, 57.23; H,6.19. Found: C, 57.14; H, 6.20.

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. concentrationconcentrated
  3. custompartitioned between chloroform (40 mL) and water (5 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (ethyl acetate: methanol, 4.4:0.6)

Sources & evidence

ORD record
ord-31482cb9c57b4bc7aba8901e8b2a321d
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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