1-Methylpyrrolidine → N-(2,6-Diethyl-4-morpholin-4-yl-phenyl)-4-methyl-benzenesulfonamide

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Reaktionsgleichung

[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([CH2:21][CH3:22])[CH:3]=1.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.C(N(CC)C(C)C)(C)C.CN1CCCC1>C(OCC)(=O)C>[CH2:8]([C:6]1[CH:7]=[C:2]([N:1]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=[C:4]([CH2:21][CH3:22])[C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

A mixture of N-(4-amino-2,6-diethyl-phenyl)-4-methyl-benzenesulfonamide (70 mg), bis-(2-bromoethyl)ether (33 μL), N,N-diisopropyl-ethylamine (115 μL) and N-methylpyrrolidine (0.3 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL), and dried over sodium sulfate. The organic phase was concentrated in vacuo to furnish 78 mg (91%) of the title compound. LC-MS (m/z) 389 (MH+); tR=2.77, (UV, ELSD) 57%, 98%. The crude product was used without further purification.

Aufarbeitung

washwashed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL)
dry with materialdried over sodium sulfate
concentrationThe organic phase was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-e0beb0048cdf4cb292bb2d7ef170d368
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08012962B2

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