2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepine-11-ylamine → (S)-2-Trifluoromethyl-11-[3-(3-methoxy-propyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

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Reaktionsgleichung

[F:1][C:2]([F:20])([F:19])[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.[CH3:21][O:22][CH2:23][CH2:24][CH2:25][C@H:26]1[CH2:31]N[CH2:29][CH2:28][NH:27]1>CN1C(=O)CCC1>[F:20][C:2]([F:1])([F:19])[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[CH2:29][CH2:28][NH:27][C@@H:26]([CH2:25][CH2:24][CH2:23][O:22][CH3:21])[CH2:31]3)[C:5]=2[CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 200 °C

Versuchsvorschrift

Add 2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepine-11-ylamine (0.438 g, 1.58 mmol), (S)-2-(3-methoxy-propyl)-piperazine (0.25 g, 1.58 mmol) in NMP (2.8 mL). Heat at 200° C. with stirring. After 2 hours, stop heating and allow the reaction mixture cool down to ambient temperature. Add brine and extract with ethyl acetate. Wash the organic solution with brine three times, dry over sodium sulfate, filter, and concentrate under reduced pressure to give crude residue. Purify the residue by flash chromatography, eluting with 2M ammonia in methanol:dichloromethane (5:95) to give the title compound: mass spectrum (m/e):419.05 (M+1).

Aufarbeitung

temperaturestop heating
temperaturecool down to ambient temperature
extractionAdd brine and extract with ethyl acetate
washWash the organic solution with brine three times
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customto give crude residue
customPurify the residue by flash chromatography
washeluting with 2M ammonia in methanol:dichloromethane (5:95)

Quellen und Nachweise

ORD-Eintrag: ord-6a07fce215914615b07282b80af7731c
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07384934B2

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