Dicyclohexylcarbodiimide → HCID 14772807, compound

HRID 1885409Notes

Reaction equation

HRID 1885409 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[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:16]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.CN(C)C=O>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([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])[CH2:26][CH2:25]2)[CH:16]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 14772796HCID 14772796, compound

Product 1

HCID 14772807HCID 14772807, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture solution of 2-(3-pyridyl)thiazolidine-4-carboxylic acid 1.7 g, 1-[3-(3-pyridyl)propyl]piperazine 1.56 g, 1-hydroxy-benzotriazole 1.3 g and N,N-dimethylformamide 20 ml was added dicyclohexylcarbodiimide 1.67 g under ice-cooling, and the mixture stirred overnight at room temperature. Ethyl acetate 50 ml was added, the precipitated dicyclohexylurea filtered off, water 30 ml added to the filtrate, the resultant solution basified with sodium hydrogen, carbonate and transferred into a separating funnel. The aqueous layer was washed with ethyl acetate, the washings combined with the ethyl acetate layer, and the resultant ethyl acetate solution washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture solution of ethyl acetate methanol (4:1) to give 860 mg of oily 1-[3-(3-pyridyl)propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine. This product was dissolved in ethanol 8 ml and after addition of fumaric acid 250 mg, the mixture allowed to stand to yield crystals. The crystals were filtered off and dried to give 580 mg of 1-]3-(3-pyridyl)propyl-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine. fumarate.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated dicyclohexylurea filtered off
  3. additionwater 30 ml added to the filtrate
  4. customtransferred into a separating funnel
  5. washThe aqueous layer was washed with ethyl acetate
  6. washthe resultant ethyl acetate solution washed with water and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluted with a mixture solution of ethyl acetate methanol (4:1)

Sources & evidence

ORD record
ord-1260b7967f9c4b1f8430049f00477eb1
Source dataset
uspto-grants-1992_09
Patent number
US05144035

Reaction notes

Loading…