Potassium Iodide → Ethyl 4-{3-{4-amino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride

HRID 1066181

Reaktionsgleichung

Reaktionsgleichung von HRID 1066181
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[O:27][CH2:28][CH2:29][CH2:30][Cl:31].Cl.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[ClH:31].[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[O:27][CH2:28][CH2:29][CH2:30][N:44]1[CH2:43][CH2:42][N:41]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[O:34][CH3:33])[CH2:46][CH2:45]1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 21197988HCID 21197988, Verbindung

Produkt 1

HCID 21197992Ethyl 4-{3-{4-amino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochlorideAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ethyl 4-{3-[4-amino-3-(3-chloropropoxy)benzoyl]indol-1-yl}butanoate (22.8 g) was dissolved in N,N-dimethylformamide (115 ml), and 1-(2-methoxyphenyl)piperazine hydrochloride (12.9 g), potassium iodide (17.1 g), potassium carbonate (17.8 g) were added to the solution. The thus-produced mixture was stirred at 90° C. for one hour. The reaction mixture was cooled and diluted with ethyl acetate (200 ml). The formed solution was sequentially washed with water and saturated brine, and dried. The solution was concentrated under reduced pressure. A′4N solution (28 ml) of hydrochloric acid in dioxane was added to the residue, and crystals so precipitated were collected by filtration. The collected crystals were recrystallized from ethanol, to thereby obtain 27.4 g of ethyl 4-{3-{4-amino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride as yellow crystals.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washThe formed solution was sequentially washed with water and saturated brine
  3. customdried
  4. concentrationThe solution was concentrated under reduced pressure
  5. additionA′4N solution (28 ml) of hydrochloric acid in dioxane was added to the residue, and crystals
  6. customso precipitated
  7. filtrationwere collected by filtration
  8. customThe collected crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4046c6a54252425a9034eb310c48b4d5
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242449B1

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