Potassium Carbonate → 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344382

Reaktionsgleichung

Reaktionsgleichung von HRID 344382
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].BrCCCCCC[C:35]1[CH:45]=[CH:44][CH:43]=[C:37]2[C:38]([NH:40][C:41](=[O:42])[C:36]=12)=O>CN(C)C=O>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:5][CH2:4][CH2:3][CH2:18][CH2:17][CH2:38][N:40]3[C:41](=[O:42])[C:36]4[C:35](=[CH:45][CH:44]=[CH:43][CH:37]=4)[C:22]3=[O:25])[CH2:15][CH2:16]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 219308536-BromohexylphthalimideHCID 667809414-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride

Produkt 1

HCID 545206764-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamideAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (8.5 g) was dissolved in dimethylformamide (100 ml). Potassium carbonate (10.5 g) and 6-bromohexylphthalimide (7.2 g) were added, and the mixture was stirred at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 4.2 g of 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b0302d1f48d04f79a5fc161d508661df
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

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