Potassium Iodide → HCID 14129813, compound

HRID 1252067Notes

Reaction equation

HRID 1252067 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11]Cl)[N:9]=1)(=[O:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+].[I-].[K+]>O1CCCC1.CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:15][CH2:14]2)[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 14931758HCID 14931758, compound2×

Product 1

HCID 14129813HCID 14129813, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Acetylamino-4-(2-chloroethyl)thiazole (1 g), 3-(4-piperidyl)indole (0.98 g), sodium hydrogen carbonate (620 mg) and potassium iodide (810 mg) were refluxed in a mixture of tetrahydrofuran (14 ml) and N,N-dimethylformamide (10 ml) for 4 hours and 10 minutes. Thereafter, with additions of 2-acetylamino-4-(2-chloroethyl)thiazole (0.5 g) three times, the mixture was further refluxed for 2 hours and 20 minutes. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. The residue was extracted with a mixture of chloroform and methanol (100 ml, 10:1 V/V) and the extract was washed successively with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and elution was carried out with a mixture of chloroform and methanol (10:1 V/V). The eluate gave 2-acetylamino-4-[2-[4-(3-indolyl)piperidino]ethyl]thiazole (500 mg).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with a mixture of chloroform and methanol (100 ml, 10:1 V/V)
  3. washthe extract was washed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was subjected to column chromatography on silica gel and elution
  7. additionwas carried out with a mixture of chloroform and methanol (10:1 V/V)

Sources & evidence

ORD record
ord-a4b61b4e6ae94bb38b0dadfc41800aba
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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