Pyridine → HCID 22340289, Verbindung

HRID 585318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585318
[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].Cl.[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1.[OH-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[CH2:46][CH2:47][N:48]([C:25]([NH:17][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[N:8]=[C:7]([CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:16]=[CH:15]4)=[O:26])[CH2:49][CH2:50]2)=[CH:41][CH:40]=1

Komponenten

9

Edukt 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 119945322-(1-Pyrrolidinylmethyl)-6-quinolinylamineHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

Produkt 1

HCID 22340289HCID 22340289, VerbindungAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the 2-(1-pyrrolidinylmethyl)-6-quinolinylamine (500 mg, 2.2 mmol) obtained in Reference Example 9 and pyridine (0.356 ml, 4.4 mmol) in tetrahydrofuran (11 ml) was added 4-nitrophenyl chloroformate (488 mg, 2.42 mmol) under ice-cooling. After stirred for 30 minutes, the reaction solution was concentrated, and dimethyl sulfoxide (11 ml) was added to the residue. 4-(4-Fluorophenyl)piperidine hydrochloride (569 mg, 2.64 mmol) and a 4N aqueous sodium hydroxide solution (0.66 ml) were added thereto at room temperature while stirring, and the mixture was stirred for 2 hours. Ethyl acetate and water were added, the mixture was extracted, the organic layer was washed with water, and concentrated, and the residue was purified by alumina column chromatography (developing solvent: ethyl acetate) to obtain the titled compound (612 mg) as a colorless powder from ethyl acetate-diisopropyl ether.

Aufarbeitung

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated
  3. additiondimethyl sulfoxide (11 ml) was added to the residue
  4. stirringat room temperature while stirring
  5. stirringthe mixture was stirred for 2 hours
  6. extractionthe mixture was extracted
  7. washthe organic layer was washed with water
  8. concentrationconcentrated
  9. customthe residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fd22fa45b95b4e3896743414d5342e53
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930185B2

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