Potassium Iodide → HCID 67424051, compound

HRID 1172224Notes

Reaction equation

HRID 1172224 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH3:24])[C:8]([C@@:10]2([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:12][C@H:11]2[CH2:13][CH2:14]Cl)=[O:9])=[CH:4][CH:3]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl.[C:36]1([C:42]2([NH:48][C:49](=[O:51])[CH3:50])[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(#N)C>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH3:24])[C:8]([C@@:10]2([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:12][C@H:11]2[CH2:13][CH2:14][N:45]2[CH2:46][CH2:47][C:42]([NH:48][C:49](=[O:51])[CH3:50])([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:43][CH2:44]2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18538563Acetamide, N-(4-phenyl-4-piperidinyl)-, monohydrochlorideHCID 67424012HCID 67424012, compound

Product 1

HCID 67424051HCID 67424051, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(1S,2S)-2-(2-Chloro-ethyl)-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide (91 mg, 0.22 mmol) is dissolved in acetonitrile (10 ml). Potassium iodide (73 mg, 0.44 mmol), potassium carbonate (91 mg, 0.66 mmol) and N-(4-Phenyl-piperidin-4-yl)-acetamide hydrochloride (67 mg, 0.26 mmol) are added. The reaction mixture is heated to reflux for 72 hours, then cooled to ambient temperature and concentrated in vacuo. The remanence is redissolved in ethyl acetate (15 ml), washed with water (10 ml), brine (10 ml), then dried over MgSO4, filtered and concentrated to an oil. The product is filtered through a plug of silica gel eluting with ethyl acetate:heptane:triethylamine (50:50:5) followed by ethyl acetate:ethanol:triethylamine (80:20:5) to furnish 70 mg (54%) of the title compound. LC/MS (m/z) 596.3 (M+H+).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 72 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe remanence is redissolved in ethyl acetate (15 ml)
  5. washwashed with water (10 ml), brine (10 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. filtrationThe product is filtered through a plug of silica gel eluting with ethyl acetate:heptane:triethylamine (50:50:5)

Sources & evidence

ORD record
ord-810f3d2d8d734567b06962bea0ac2c2f
Source dataset
uspto-grants-2010_11
Patent number
US07834008B2

Reaction notes

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