1-Methylpiperazine → 1-Methyl-4-({(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl)piperazine

HRID 853913Notizen

Reaktionsgleichung

CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])(=O)=O)=CC=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOCC>[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[CH2:31][CH2:30]1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a solution of {(2S)-1-[(4-methylphenyl)sulfonyl]pyrrolidin-2-yl}methyl 4-methylbenzenesulfonate (9.427 g, 23.13 mmol) (Tetrahedron, 43(14), 3289, 1987) in toluene (150 mL), was added n-methyl-piperazine (12.8 mL, 115.65 mmol) and DBU (0.352 g, 2.313 mmol) and the solution was stirred at 140° C. overnight. The reaction was then diluted with ether and washed with brine. The organic layer was dried over Na2SO4, filtered, concentrated and purified on Biotage flash 40M cartridge silica gel eluting with CH2Cl2/CH3OH/NH4OH (95.5/3/1.5) to give an off white solid (2.570 g, 55% ). NMR (400 Mz, DMSO-d6): consistent. MS (ES+) m/z 338.1 [M+H]. m.p.: 96.5-97.7° C. Reference: (Tetrahedron, 43(14), 3289, 1987).

Aufarbeitung

washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified on Biotage flash 40M cartridge silica gel eluting with CH2Cl2/CH3OH/NH4OH (95.5/3/1.5)

Quellen und Nachweise

ORD-Eintrag: ord-fef5cb0c18be48b29be5920d6bae3773
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07256198B2

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