Piperidine → N-[3-(2,2-dimethylchroman-6-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]acetamide

HRID 24390

Reaktionsgleichung

Reaktionsgleichung von HRID 24390
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][C:10](=[O:14])[NH:11]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:15][C:16]1([CH3:28])[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:26]=O)[CH:22]=2)[O:17]1.N1CCCCC1>O>[CH3:15][C:16]1([CH3:28])[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:26]=[C:9]3[C:8]4[C:12](=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=4)[NH:11][C:10]3=[O:14])[CH:22]=2)[O:17]1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 17977512,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-carbaldehydeHCID 2749839N-(2-Oxoindolin-6-yl)acetamide

Produkt 1

HCID 57040241N-[3-(2,2-dimethylchroman-6-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]acetamideAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 6-acetamido-2-oxindole (285 mg), 2,2-dimethylchroman-6-carboxaldehyde (285 mg) and piperidine (0.2 ml) was stirred at 90° C. overnight. The reaction mixture was cooled and diluted with 20 ml of water. The sticky solid which formed was filtered and chromatographed (2% ethanol in ethyl acetate) to give 240 mg (44%) of N-[3-(2,2-dimethylchroman-6-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]acetamide as an orange red solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe sticky solid which formed
  3. filtrationwas filtered
  4. customchromatographed (2% ethanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-01a3a2ad64bf410eb46cf49e157ea541
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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