Piperidine → HCID 54352759, Verbindung

HRID 2120239

Reaktionsgleichung

Reaktionsgleichung von HRID 2120239
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1.N1CCCCC1>C(O)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[CH:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[C:17]([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[CH:18]=1)[C:7](=[O:13])[NH:8]2

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 109430044-(2-Hydroxyethyl)indolin-2-oneHCID 219810244-Methoxy-3-(thiophen-2-yl)benzaldehyde

Produkt 1

HCID 54352759HCID 54352759, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.6 g, 9.2 mmol), 4-methoxy-3-thiophen-2-yl-benzaldehyde (2 g, 9.2 mmol) and piperidine (4.5 mL, 85 mmol) in ethanol (46 mL) was heated to reflux for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 1.63 g (47%) of 4-(2-hydroxy-ethyl)-3-(4-methoxy-3-thiophen-2-yl-benzylidene)-1,3-dihydro-indol-2-one as a yellow orange solid. 1HNMR (300 MHz, DMSO-d6) δ 10.53 (s, br, 1H, NH), 8.73 (d, J=2.1 Hz, 1H), 8.10 (dd, J=2.2 & 9.1 Hz, 1H), 7.74 (s, 1H, H-vinyl), 7.56-7.65 (m, 2H), 7.07-7.22 (m, 3H), 6.81 (d, J=7.5 Hz, 1H), 6.68 (dd, J=0.6, 7.5 Hz, 1H), 4.87 (t, J=4.5 Hz, 1H, OH), 3.97 (s, 3H, OCH3), 3.68-3.75 (m, 2H, CH2CH2OH), 3.09 (t, J=4.5 Hz, 2H, CH2CH2OH).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was chromatographed on a column of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-026f27878bb8434eb2bd152067b6cb4c
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06689806B1

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