Water → 1-[1-{4-[5-(4-Trifluoroacetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril

HRID 1463312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463312
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:32]=[CH:31][C:11]([C:12]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][C:21]3=[O:22])[CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1.[F:33][C:34]([F:45])([F:44])[C:35]([NH:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:36].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:45][C:34]([F:33])([F:44])[C:35]([NH:37][CH:38]1[CH2:43][CH2:42][N:41]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:32]=[CH:31][C:11]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:24][CH2:23][C:21]4=[O:22])[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH2:40][CH2:39]1)=[O:36]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamideHCID 189607521-{1-[4-(5-Bromopentyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril

Produkt 1

HCID 189607451-[1-{4-[5-(4-Trifluoroacetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyrilAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-{1-[4-(5-Bromopentyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (2 g) and 4-trifluoroacetylaminopiperidine (2 g) are dissolved in dimethylformamide (40 ml), and thereto is added potassium carbonate (2 g) and the mixture is stirred overnight. The reaction mixture is poured into water, and the mixture is extracted with toluene/ethyl acetate (1:1), dried over magnesium sulfate, and purified by silica gel column chromatography (eluent; dichloromethane: methanol=50:1) to give 1-[1-{4-[5-(4-trifluoroacetylamino-1-piperidinyl)pentyloxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (2 g) as colorless oil.

Aufarbeitung

  1. extractionthe mixture is extracted with toluene/ethyl acetate (1:1)
  2. dry with materialdried over magnesium sulfate
  3. custompurified by silica gel column chromatography (eluent; dichloromethane: methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb25a16a1366425dbb2b683487109bbb
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300513

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