Water → HCID 11952785, Verbindung

HRID 1354062

Reaktionsgleichung

Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C.Cl[CH2:26][CH2:27][CH2:28][C:29]([N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32]1)=[O:30].O>CN(C)C=O>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:26][CH2:27][CH2:28][C:29]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][CH2:32]2)=[O:30])[CH2:12][CH2:11]1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

A mixture of 1-(2,3-dichlorophenyl)piperazine, hydrochloride (8.0 g) and diisopropylethylamine (10 mL) in dimethyl formamide (50 mL) was heated to 45° C. followed by the addition of 4-chloro-1-(2,3-dihydro-1H-indol-1-yl)butan-1-one (6.7 g). The resulting mixture was heated at 100° C. for 6 h, cooled to room temperature and poured into water. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried (MgSO4), filtered and evaporated in vacuo to give a black oil (14.2 g). The oil was crystallised from acetone, and the formed crystals were recrystallised from ethanol to give a white crystalline material (3.8 g). Mp 134–136° C. 1H NMR (CDCl3): 1.90–2.05 (m, 2H); 2.45–2.60 (m, 4H); 2.65 (s, 4H); 3.00 (s, 4H); 3.20 (t, 2H); 4.10 (t, 2H); 6.90 (d, 1H); 7.00 (t, 1H); 7.05–7–25 (m, 4H); 8.25 (d, 1H). MS m/z: 418 (MH+), 299, 228, 188.

Aufarbeitung

temperatureThe resulting mixture was heated at 100° C. for 6 h
temperaturecooled to room temperature
extractionThe aqueous phase was extracted with diethyl ether
dry with materialthe combined organic phases were dried (MgSO4)
filtrationfiltered
customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-2148663ae566470eac44bfb98dfff919
Quelldatensatz: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07223765B2

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