Piperidine → N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide

HRID 24409

Reaktionsgleichung

Reaktionsgleichung von HRID 24409
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:22]([NH:25][C:26]1[CH:34]=[C:33]2[C:29]([CH2:30][C:31](=[O:35])[NH:32]2)=[CH:28][CH:27]=1)(=[O:24])[CH3:23].N1CCCCC1.C(OCC)(=O)C>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:8]=[C:30]1[C:29]2[C:33](=[CH:34][C:26]([NH:25][C:22](=[O:24])[CH3:23])=[CH:27][CH:28]=2)[NH:32][C:31]1=[O:35])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 2749839N-(2-Oxoindolin-6-yl)acetamideHCID 225710723-Tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde

Produkt 1

HCID 53907275N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-tert-butyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.25 g), 6-acetamido-2-oxindole (0.16 g) and piperidine (0.43 ml) in ethanol (3 ml) was held in a sealed tube at 100° C. for 12 hours. The reaction was cooled, added to ethyl acetate (250 ml), washed with 1N hydrochloric acid (100 ml) and brine (100 ml), dried with magnesium sulfate and concentrated. Some product went into the acid wash, so this was basified with solid sodium bicarbonate to pH 9 and extracted with ethyl acetate (2×150 ml). The organic layers were dried over magnesium sulfate, combined with the oil from the first crop of product and concentrated. Chromatography (silica, 40% ethyl acetate followed by 5-10% methanol/methylene chloride) afforded 100 mg (27%) of N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. washwashed with 1N hydrochloric acid (100 ml) and brine (100 ml)
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. washwash
  6. extractionextracted with ethyl acetate (2×150 ml)
  7. dry with materialThe organic layers were dried over magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1544f1db1a5e47a6b52225f05d1fcb4c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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