Dimethyl Sulfoxide → 2-Methyl-11-(4-methyl-piperazin-1-yl)-3-methyl-5H-dibenzo[b,e][1,4]diazepine

HRID 1350514

Reaktionsgleichung

Cl.[CH3:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([NH2:12])[C:5]=2[CH:4]=1.[CH3:19][N:20]1[CH2:25][CH2:24]N[CH2:22][CH2:21]1.[CH:26](N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:3]1[C:18]([CH3:26])=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([N:12]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[C:5]=2[CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Combine 2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (600.0 mg, 2.31 mmol), N-methylpiperazine (1.39 g, 13.86 mmol), N,N-diisopropylethylamine (298.6 mg, 2.31 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 110° C. After 48 hours, cool the mixture to ambient temperature and stir it overnight. Dilute the mixture with ethyl acetate and wash the organic layer with 0.1N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 550.5 mg (78%) of a tan foam: mp 170°–177°, dec; mass spectrum (ion spray): m/z=307.2 (M+1).

Aufarbeitung

temperaturecool the mixture to ambient temperature
stirringstir it overnight
washwash the organic layer with 0.1N NaOH and brine
dry with materialDry (sodium sulfate)
concentrationconcentrate the organic layer to residue
customPurify the residue on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-88e54ce9c03740f3a94b95b547bf4700
Quelldatensatz: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07214673B2

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