Potassium Iodide → HCID 70109593, compound

HRID 1279344Notes

Reaction equation

HRID 1279344 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]1[O:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[N:10]([C:21](=[O:34])[C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)[CH2:9]1)(=O)=O.Cl.[C:36]1([C:42]2([C:48]([NH2:50])=[O:49])[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])O.[Na+].[I-].[K+].[Cl-].[Na+]>CN(C)C=O>[Cl:20][C:15]1[CH:14]=[C:13]([CH:11]2[N:10]([C:21](=[O:34])[C:22]3[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=3)[CH2:9][C@@H:8]([CH2:7][CH2:6][N:45]3[CH2:44][CH2:43][C:42]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([C:48]([NH2:50])=[O:49])[CH2:47][CH2:46]3)[O:12]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 131722207HCID 131722207, compound

Product 1

HCID 70109593HCID 70109593, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

150 mg (0.28 mmole) of 2-[(5R)-(3,4-dichlorophenyl)-3-(3,4,5-trimethoxybenzoyl)oxazolidin-5-yl]ethanol methanesulfonate [prepared as described in step (g) above] and 75 mg (0.31 mmole) of 4-phenylpiperidine-4-carboxamide hydrochloride were dissolved in 3 ml of anhydrous dimethylformamide, and 71 mg (0.85 mmole) of sodium hydrogencarbonate and 70 mg (0.42 mmole) of potassium iodide were added to the resulting solution. The mixture was then heated under a nitrogen atmosphere at 80° C. for 6 hours. At the end of this time, 50 ml of a saturated aqueous solution of sodium chloride were added to the reaction mixture, which was then extracted three times, each time with 50 ml of ethyl acetate. The combined organic extracts were then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel thin-layer chromatography, using a 10:1 by volume mixture of methylene chloride and methanol as the developing solvent, to give 127 mg (yield 71%) of the title compound as a white amorphous substance.

Workup

  1. extractionwas then extracted three times
  2. dry with materialThe combined organic extracts were then dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe resulting residue was purified by silica gel thin-layer chromatography
  5. additionby volume mixture of methylene chloride and methanol as the developing solvent

Sources & evidence

ORD record
ord-eccc4649690e4bb69fc47e02d4f7c8e3
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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