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2,6-dichloro-N'-hydroxybenzene-1-carboximidamide → 1-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 551793
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551793
[N:1]1([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71](=[N:73]O)[NH2:72]>O.CN(C)C=O>[Cl:63][C:64]1[CH:69]=[CH:68][CH:67]=[C:66]([Cl:70])[C:65]=1[C:71]1[N:73]=[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([C:11]([N:1]3[C:2]4[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:8][CH2:9][CH2:10]3)=[O:12])[CH2:14][CH2:15]2)[O:20][N:72]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 319562,6-dichloro-N'-hydroxybenzene-1-carboximidamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 285131921-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 24852912
1-({4-[3-(2,6-Dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline
Ausbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.3 g of 1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)piperidine-4-carboxylic acid, 11 ml of dimethylformamide, 0.67 g of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 0.028 g of 1-hydroxybenzotriazole, 0.91 ml of diisopropylethylamine and then 0.32 g of 2,6-dichloro-N′-hydroxybenzenecarboximidamide are introduced into a 100 ml round-bottomed flask. The reaction medium is stirred at ambient temperature for 1 h 30 and then heated at 95° C. for 20 hours. Water is added and the mixture is extracted with ethyl acetate. The organic phase is washed three times with water and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1. 0.18 g of 1-({4-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline is obtained.

Aufarbeitung

  1. temperatureheated at 95° C. for 20 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic phase is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with a heptane/ethyl acetate gradient from 0/1 to 1/1

Quellen und Nachweise

ORD-Eintrag
ord-dbda138097cc4f2faacfcf8f1e139397
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947834B2

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