Potassium Iodide → HCID 69100589, compound

HRID 2115075Notes

Reaction equation

HRID 2115075 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9]2)=[O:4].[I-].[K+].C(N(CC)CC)C.[CH2:25]([CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[CH2:25]([CH:32]1[CH2:37][CH2:36][N:35]([CH2:2][C:3]([NH:5][C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9]3)=[O:4])[CH2:34][CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 317384-BenzylpiperidineHCID 533102722-chloro-N-(2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 69100589HCID 69100589, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.9 g (4 mmol) of 2-chloro-N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide, 0.7 g (4 mmol) of potassium iodide, 0.6 ml (4 mmol) of triethylamine, 0.53 ml (3 mmol) of 4-benzyl-piperidine 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 treated with diethylether and the precipitated crystals are filtered off to yield 0.7 g (64%) of the title compound. Melting Point: 176-180° 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. additionthe residue is treated with diethylether
  9. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-2f2f2685b9c94a5885ccef5aa2246dfc
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

Loading…