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Water → N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamine

HRID 642962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 642962
[H-].[Na+].[CH:3]1([N:9]([CH3:13])[CH2:10][CH2:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:14]([Sn:18]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19]I)[CH2:15][CH2:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH3:13][N:9]([CH2:10][CH2:11][O:12][CH2:19][Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2775822-(Cyclohexylmethylamino)ethanolHCID 10862926Tributyl(iodomethyl)stannane

Produkt 1

HCID 59259719N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%).

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled at 0° C. (external temperature)
  2. stirringthe reaction mixture was stirred at 60° C. for 1 hour
  3. additionwas added
  4. customthe reaction
  5. customthe organic layer was separated
  6. washAfter the organic layer was washed with water
  7. distillationan aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-210dbaacbcd64b4dbdd1bdd888419e6a
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07696347B2

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