Potassium Carbonate → 3-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-1H-indole, hydrochloride

HRID 1791172

反応式

HRID 1791172 の反応式
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(#N)C>[ClH:20].[Cl:20][C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH2:30][CH2:29]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 8518331-(2,3-Dichlorophenyl)piperazineHCID 100371923-(3-bromopropyl)-1H-indole

生成物 1

HCID 98670593-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-1H-indole, hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3-(3-bromopropyl)-1H-indole (1.19 g), potassium carbonate (1.4 g) and 1-(2,3-dichlorophenyl)piperazine (1.27 g) in anhydrous acetonitrile (10 mL) was boiled under reflux for 5 h and cooled to room temperature. The mixture was added silicagel (7 g), and the solvent was evaporated in vacuo. The compound was purified by flash chromatography on silicagel (eluent:ethylacetate/heptane/triethylamine 49:49:2). Fractions containing the compound were combined and evaporated in vacuo. Recrystallisation from acetonitrile gave the title compound as a white crystalline material. The compound was precipitated as the hydrochloride salt (1 g). Mp 241–242° C. 1H NMR (DMSO-d6): 2.10–2.2,5 (m, 2H); 2.75 (t, 2H); 3.10–3.30 (m, 6H); 3.40 (t, 2H); 3.60 (d, 2H); 7.00 (t, 1H); 7.05 (t, 1H); 7.15 (d, 1H); 7.25 (s, 1H); 7.30–7.40 (m, 3H); 7.55 (d, 1H); 10.90 (b s, 1H); 11.40 (b s, 1H). Ms m/z: 388 (MH+).

後処理

  1. temperatureunder reflux for 5 h
  2. additionThe mixture was added silicagel (7 g)
  3. customthe solvent was evaporated in vacuo
  4. customThe compound was purified by flash chromatography on silicagel (eluent:ethylacetate/heptane/triethylamine 49:49:2)
  5. additionFractions containing the compound
  6. customevaporated in vacuo
  7. customRecrystallisation from acetonitrile

出典と根拠

ORDレコード
ord-5336bacc510e450986497bcfc85c5b3a
出典データセット
uspto-grants-2006_07
特許番号
US07074796B2

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