Dicyclohexylcarbodiimide → 1-[3-(1-Imidazolyl)propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine

HRID 1885407Notes

Reaction equation

HRID 1885407 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[N:15]1([CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:19]=[CH:18][N:17]=[CH:16]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.CO.C(OCC)(=O)C.CN(C)C=O>[N:15]1([CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:12]([CH:10]3[CH2:9][S:8][CH:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[NH:11]3)=[O:14])[CH2:25][CH2:24]2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 147727971-[3-(1-Imidazolyl)propyl]piperazine

Product 1

HCID 147728011-[3-(1-Imidazolyl)propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazineYield 53.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-(3-pyridyl)thiazolidine-4-carboxylic acid 630 mg, 1-[3-(1-imidazolyl)propyl]piperazine 580 mg, 1-hydroxybenztriazole 410 mg and N,N-dimethylformamide 15 ml was added dicyclohexylcarbodiimide 620 mg under ice-cooling and then stirred overnight at room temperature. Ethyl acetate 100 ml was added to the solution, the resultant unsoluble matter filtered off and the solution washed with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride in succession. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, ethyl acetate added to the residue, the unsoluble matter filtered off and the solution concentrated to dryness under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (eluent: 20% methanol-ethyl acetate) to give an oily product. This was dissolved in ethyl acetate 30 ml, 2N hydrogen chloridedioxane 4 ml added and the precipitated powder filtered off to give 620 mg of 1-[3-(1-imidazolyl)propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine. 4 hydrochloride.

Workup

  1. temperaturecooling
  2. filtrationthe resultant unsoluble matter filtered off
  3. washthe solution washed with saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride in succession
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure, ethyl acetate
  6. additionadded to the residue
  7. filtrationthe unsoluble matter filtered off
  8. concentrationthe solution concentrated to dryness under reduced pressure
  9. customThe residue thus obtained
  10. customto give an oily product
  11. additionadded
  12. filtrationthe precipitated powder filtered off

Sources & evidence

ORD record
ord-25be6413dd7e4b58bc4feaafbc66f0f7
Source dataset
uspto-grants-1992_09
Patent number
US05144035

Reaction notes

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