Potassium Carbonate → HCID 21093826, compound

HRID 1767577Notes

Reaction equation

HRID 1767577 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:8].[C:21]1(=[O:27])[NH:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O1CCOCC1>[Cl:20][C:5]1[CH:4]=[CH:3][C:2]([N:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:27])=[CH:19][C:6]=1[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 126652-PiperidoneHCID 21093909HCID 21093909, compound

Product 1

HCID 21093826HCID 21093826, compoundYield 1.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-2-chloro-N-[2-(2-chloro-phenyl)-ethyl]-benzamide (200 mg, 0.536 mmol), δ-valerolactam (106 mg, 1.07 mmol), potassium carbonate (156 mg, 1.13 mmol), dioxane (1 ml, purged with nitrogen), and copper (I) iodide (5 mg) in an oven-dried round bottom flask equipped with a reflux condenser under a nitrogen atmosphere was heated in an oil bath at 120–125° C. After 21 hours the mixture was cooled to room temperature, filtered through a pad of silica gel and concentrated under reduced pressure to give 50 mg of crude product. Purification by preparative HPLC (Shimadsu LC-8A preparative liquid chromatograph) eluting with a gradient of 0.1% aqueous formic acid in acetonitrile provided 2.5 mg of the title compound as a colorless amorphous solid. Mass Spectrum (ES+) 391.6; LC retention time=2.3 minutes (using the LC/MS and method outlined for the examples in Table 1).

Workup

  1. customequipped with a reflux condenser under a nitrogen atmosphere
  2. temperaturewas heated in an oil bath at 120–125° C
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated under reduced pressure
  5. customto give 50 mg of crude product
  6. customPurification by preparative HPLC (Shimadsu LC-8A preparative liquid chromatograph)
  7. washeluting with a gradient of 0.1% aqueous formic acid in acetonitrile

Sources & evidence

ORD record
ord-b7e29e6d8b394bc79e702b51d6865dc6
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

Loading…