Aluminum(III) Chloride → 1-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-indole, Hydrochloride

HRID 1791171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791171
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Cl-].[Cl-].[Al+3].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]([N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)=O)[CH2:21][CH2:20]1>O1CCCC1>[ClH:11].[Cl:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)[CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 6451240Aluminum(III) ChlorideHCID 113271493-[4-(2,3-Dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one2×HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1317258501-{3-[4-(2,3-Dichlorophenyl)piperazin-1-yl]propyl}-2,3-dihydro-1H-indole, Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Lithium aluminium hydride (1.8 g) was suspended in tetrahydrofuran (30 mL) at 0° C., and the suspension was added a solution of aluminium trichloride (1.8 g) in tetrahydrofuran (30 mL) at 0–5° C. over 15 min. To this mixture, a solution of 1a, 3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-1-(2,3-dihydro-1H-indol-1-yl)propan-1-one (5 g) in tetrahydrofuran (50 mL) was added at a temperature of 0–10° C. The resulting mixture was stirred for 30 min at 5° C. and then for 2 h at room temperature. The reaction mixture was quenched with water and sodium hydroxide (28%) and filtered. The organic phase was evaporated to dryness in vacuo, and the title compound was precipitated as the hydrochloride salt and recrystallised from ethanol (3.8 g). Mp 214–226° C. 1H NMR (DMSO-d6): 2.05–2.20 (m, 2H); 2.95 (t, 2H); 3.10–3.35 (m, 8H); 3.35–3.50 (m, 4H); 3.60 (d, 2H); 6.70 (b s, 2H); 7.05 (t, 1H); 7.10 (d, 1H); 7.20 (d, 1H); 7.30–7.40 (m, 2H); 11.45 (b s). MS m/z: 390 (MH+), 271, 132.

Aufarbeitung

  1. waitfor 2 h at room temperature
  2. customThe reaction mixture was quenched with water and sodium hydroxide (28%)
  3. filtrationfiltered
  4. customThe organic phase was evaporated to dryness in vacuo
  5. customthe title compound was precipitated as the hydrochloride salt
  6. customrecrystallised from ethanol (3.8 g)

Quellen und Nachweise

ORD-Eintrag
ord-d38d6c6f0c5a41f987fe4567dbc73965
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074796B2

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