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Hydrochloric Acid → 1-[3-(2-Furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine

HRID 1709286
Notes
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Reaction equation

HRID 1709286 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.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Cl.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CN(C)C=O>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:12]([CH:10]2[CH2:9][S:8][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:11]2)=[O:14])[CH2:25][CH2:24]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 14772793
1-[3-(2-Furyl)propyl]piperazine

Product 1

HCID 147728051-[3-(2-Furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture solution of 2-(3-pyridyl)thiazolidine-4-carboxylic acid 0.5 g, 1-[3-(2-furyl)propyl]piperazine.2 hydrochloride 0.54 g and N,N-dimethylformamide 5 ml were added N-methylmorpholine 0.2 g and N,N-dimethylformamide 2 ml under ice-cooling. Further 1-hydroxybenzotriazole 0.4 g was added, then dicyclohexylcarbodiimide 0.46 g added and the mixture was stirred overnight at room temperature. Ethyl acetate 50 ml and water 10 ml were added, the solution basified with sodium hydrogen carbonate, the insoluble matter filtered off and the solution transferred into a separtating funnel. The aqueous layer was extracted with ethyl acetate, the extract combined with the organic layer, washed with water and saturated aqueous sodium chloride solution, 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 0.25 g of oily 1-[3-(2-furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine.

Workup

  1. temperaturecooling
  2. filtrationthe insoluble matter filtered off
  3. customthe solution transferred into a separtating funnel
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixture solution of ethyl acetate - methanol (4:1)

Sources & evidence

ORD record
ord-005904139d7c4257888c34a4a684eccb
Source dataset
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04948795

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes