Triethylamine → 1-(1-(2,4-Dimethoxybenzoyl)-4-piperidyl)indol-2-one

HRID 1377688

Reaktionsgleichung

Reaktionsgleichung von HRID 1377688
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[CH3:17][O:18][C:19]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:17][O:18][C:19]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=1[C:21]([N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[O:16])[CH2:3][CH2:2]1)=[O:22]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 27347192,4-Dimethoxybenzoyl chlorideHCID 27611521-Piperidin-4-yl-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 229146571-(1-(2,4-Dimethoxybenzoyl)-4-piperidyl)indol-2-oneAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(4-Piperidyl)indol-2-one (53 mg, 0.245 mmole), 2,4-dimethoxybenzoyl chloride (54 mg, 0.27 mmole), and 38 mL (0.27 mmole) triethylamine were mixed in 4 ml of chloroform at 0° C. The reaction mixture was stirred at 0° C. for 5 minutes and then at 23° C. for 15 minutes during which time the pH was adjusted to 7.5 with triethylamine. The reaction mixture was concentrated under reduced pressure and the residue was purified by preparative thick layer chromatography (CHCl3 --CH3OH--NH4OH; 95:5:0.5) to yield 42 mg of the title compound: m.p. 88°-93° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by preparative thick layer chromatography (CHCl3 --CH3OH--NH4OH; 95:5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-75a0481253b94f3ea3f76576417ad1fe
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665719

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