1-Aminopiperidine → 3-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-N-(piperidin-1-yl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine

HRID 490673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490673
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=O)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:38][N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH:38][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)=[N:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 166581-AminopiperidineHCID 24819Phosphorus pentachlorideHCID 113748943-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl4,5-dihydro-1H-pyrazole-1-carboxamide

Produkt 1

HCID 688430033-(4-chlorophenyl)-N'-((4-chlorophenyl)sulfonyl)-N-(piperidin-1-yl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidineAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

Part B: A mixture of 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (1.42 gram, 3.00 mmol) and phosphorus pentachloride (PCl5) (0.63 gram, 3.03 mmol) in chlorobenzene (15 mL) is heated at reflux temperature for 1 hour. After thorough concentration in vacuo, the formed 3-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboximidoyl chloride is suspended in dry dichloromethane (30 mL) and reacted with 1-aminopiperidine (1.08 mL, 10.0 mmol). After stirring at room temperature for 16 hours, the mixture is twice washed with water and concentrated in vacuo. The residue is crystallised from methyl-t-butyl ether (MTBE) to give pure 3-(4-chlorophenyl)-N′-((4-chlorophenyl)sulfonyl)-N-(piperidin-1-yl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine (0.57 gram, 34% yield). Melting point (MP): 213-214° C. MS ESI+: 556 (MH+).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 1 hour
  3. concentrationAfter thorough concentration in vacuo
  4. washthe mixture is twice washed with water
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallised from methyl-t-butyl ether (MTBE)

Quellen und Nachweise

ORD-Eintrag
ord-80d44b4fac314e8e80451f98b8cc4468
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528162B2

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