2-Chloroethanol → 3-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2-hydroxyethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamide

HRID 32429

Reaktionsgleichung

Reaktionsgleichung von HRID 32429
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:40][CH2:41][OH:42]>CCO.O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][CH:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[CH2:15][O:16][CH2:17][CH:18]3[CH2:23][CH2:22][N:21]([CH2:40][CH2:41][OH:42])[CH2:20][CH2:19]3)=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 342-ChloroethanolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 693078883-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide

Produkt 1

HCID 693105593-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2-hydroxyethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (200 mg, 0.45 mmol) in 5 mL of EtOH was added potassium carbonate (247 mg, 1.8 mmol), potassium iodide (224 mg, 1.4 mmol) and 2-chloroethanol (0.09 mL, 1.4 mmol). The reaction was allowed to stir at room temperature overnight after which time water was added and the resulting precipitate was isolated by filtration. Purification of the filtrate (SiO2: 10:0.5 EtOAc:isopropylamine) provided 70 mg (32%) of the title compound.

Aufarbeitung

  1. additionwas added
  2. customthe resulting precipitate was isolated by filtration
  3. customPurification of the filtrate (SiO2: 10:0.5 EtOAc:isopropylamine)

Quellen und Nachweise

ORD-Eintrag
ord-820aeae5bdb84ba49a24b28cd989f7d3
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427632B2

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