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

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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][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28]N[CH2:26][CH2:25][NH:24]1.C(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[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]([N:12]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]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), (S)-2-(2-methoxy-ethyl)-piperazine (666.3 mg, 4.62 mmol), N,N-diisopropylethylamine (298.6 mg, 2.31 mmol), DMSO (1.0 ml), and toluene (4.0 ml) and stir and heat the mixture at 110° C. After 46 hours, cool the mixture to ambient temperature and dilute with ethyl acetate. 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 425.5 mg (53%) of a yellow foam: mp 63° C., dec; mass spectrum (ion spray): m/z 351.2 (M+1).

Aufarbeitung

temperaturecool the mixture to ambient temperature
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-2fb76ec4520b4c85abf1914780450688
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07384934B2

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