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

HRID 1885408
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HRID 1885408 반응식
[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
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참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 147727931-[3-(2-Furyl)propyl]piperazine

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-730f1491885e43ac879e4fc6b9420fe1
출처 데이터셋
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05144035

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