Chlorodiphenylmethane → Ethyl 4-{3-{4-diphenylmethylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate

HRID 1066182

Reaktionsgleichung

Reaktionsgleichung von HRID 1066182
Cl.[NH2:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=2)=[O:8])=[CH:5][C:4]=1[O:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:44][CH3:45])[CH2:34][CH2:33]1.[C:46]1([CH:52](Cl)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:46]1([CH:52]([NH:2][C:3]2[CH:27]=[CH:26][C:6]([C:7]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=3)=[O:8])=[CH:5][C:4]=2[O:28][CH2:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][N:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[O:44][CH3:45])[CH2:34][CH2:33]2)[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Komponenten

6

Edukt 3

HCID 7035ChlorodiphenylmethaneHCID 11430Potassium CarbonateHCID 21197992HCID 21197992, Verbindung

Produkt 1

HCID 15513821Ethyl 4-{3-{4-diphenylmethylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ethyl 4-{3-{4-amino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate hydrochloride (2.0 g) was dissolved in N,N-dimethylformamide (10 ml), and diphenylmethyl chloride (1.2 ml) and potassium carbonate (1.3 g) were added to the solution. The mixture was stirred at 90° C. for five hours. The reaction mixture was cooled and diluted with ethyl acetate (200 ml). The resultant mixture was sequentially washed with water and saturated brine, and dried and evaporated under reduced pressure. The resultant residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby obtain 1.13 g of ethyl 4-{3-{4-diphenylmethylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}benzoyl}indol-1-yl}butanoate as a pale yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washThe resultant mixture was sequentially washed with water and saturated brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f7990c3e9f37481390577c253d48e9fb
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242449B1

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