Potassium Iodide → HCID 10221566, compound

HRID 2115074Notes

Reaction equation

HRID 2115074 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=1)=[O:4].[I-].[K+].C(N(CC)CC)C.Cl.[F:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:29][CH:28]=1>C(#N)C>[F:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][CH:32]2[CH2:33][CH2:34][N:35]([CH2:2][C:3]([NH:5][C:6]3[CH:15]=[CH:14][C:9]4[NH:10][C:11](=[O:13])[O:12][C:8]=4[CH:7]=3)=[O:4])[CH2:36][CH2:37]2)=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 1132892HCID 1132892, compoundHCID 170394924-[(4-Fluorophenyl)methyl]piperidine hydrochloride

Product 1

HCID 10221566HCID 10221566, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.91 g (4 mmol) of 2-chloro-N-(2-oxo-2,3-dihydro-benzoxazol-6-yl)-acetamide, 0.7 g (4 mmol) of potassium iodide, 1.2 ml (8 mmol) of triethylamine, 0.7 g (3 mmol) of 4-(4-fluoro-benzyl)-piperidine hydrochloride and 50 ml of acetonitrile is refluxed for 20 hours. The reaction mixture is concentrated and 30 ml of water and 30 ml of chloroform are added to the residue. The organic layer is separated and the water phase is extracted three times with 10 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 adsorbent (Merck) and chloroform methanol=97:3 as eluent to yield 0.3 g (26%) of the title compound. Melting Point: 232-234° C. (diethylether)

Workup

  1. temperatureis refluxed for 20 hours
  2. concentrationThe reaction mixture is concentrated
  3. addition30 ml of water and 30 ml of chloroform are added to the residue
  4. customThe organic layer is separated
  5. extractionthe water phase is extracted three times with 10 ml of chloroform
  6. dry with materialThe combined organic layers are dried over sodium sulfate
  7. concentrationconcentrated
  8. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-e048cab561724f868d446bb852860ef3
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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