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Diethyl Ether → N-(3-{3-[(E)-2-hexenyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 1826364
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1826364
[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:7]2[CH:3]1[CH2:4][NH:5][CH2:6]2.C(=O)([O-])O.[Na+].Br[CH2:25][C:26]#[C:27][CH2:28][CH2:29][CH3:30].C(OCC)C>O>[NH3:5].[CH2:25]([N:5]1[CH2:6][CH:7]2[CH:3]([C:2]2([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH3:1])[CH2:4]1)/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH3:30]
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Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 123525931-Bromohex-2-yneHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

Produkt 2

HCID 222AmmoniaHCID 22141346N-(3-{3-[(E)-2-hexenyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide
Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 57 mg, 0.19 mmol) dissolved in N,N-dimethylformnamide (2 ml) was added sodium hydrogen carbonate (630 mg, 7.52 mmol) and 1-bromo-2-hexyne (H. A. J. Charles, and R. J. Batten, J. Chem. Soc., Perkin Trans 1, 1987, 1999, 33 mg, 0.2 mmol) and the reaction mixture was heated at 50° C. for 20 h. After cooling diethyl ether (5 ml) and water (7 ml) were added and the reaction mixture was stirred vigorously for 5 min. The phases were separated and the aqueous layer was further extracted with diethyl ether (2×5 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residual oil was purified by flash column chromatography using a Sep-Pak™ cartridge packed with silica gel (5 g) eluting with dichloromethane:ethanol:0.88 ammonia solution (200:8:1) to afford the title compound as an oil (33 mg, 50%).

Aufarbeitung

  1. additionwere added
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with diethyl ether (2×5 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by flash column chromatography
  8. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-0156b5cc82814ef9b52a2bcf228fadeb
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07049444B2

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