Sodium Iodide → 1-[2-(1-Adamantyl)ethyl]-1-[2-[N-(2-methoxyethyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]urea

HRID 1393182

Reaktionsgleichung

Reaktionsgleichung von HRID 1393182
[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][NH:28][CH3:29])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:38][O:39][CH2:40][CH2:41]Cl>O.C(OCC)C.CN(C)C=O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][N:28]([CH2:41][CH2:40][O:39][CH3:38])[CH3:29])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 121366481-[2-(1-Adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea

Produkt 1

HCID 121366521-[2-(1-Adamantyl)ethyl]-1-[2-[N-(2-methoxyethyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]ureaAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To N,N-dimethylformamide (20 ml) were added 1-[2-(1-adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea (1.50 g, 3.76 mmol), which was a free base of Compound No. 3-1, potassium carbonate (1.56 g, 11.3 mmol) and sodium iodide (1.69 g, 11.3 mmol) at room temperature, then 2-chloroethyl methyl ether (412 μl, 4.51 mmol) was added to the mixture, and the whole was heated at 80° C. The whole was stirred overnight, diethyl ether (50 ml) and water (100 ml) were added to the reaction mixture, and the whole was extracted. The obtained organic layer was washed with water (100 ml) and a saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 552 mg (32.1%) of the titled compound as a pale yellow oily matter.

Aufarbeitung

  1. extractionthe whole was extracted
  2. washThe obtained organic layer was washed with water (100 ml)
  3. dry with materiala saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ae1b16e2d4024b55a0d2d7a7c7ee9df0
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345064B2

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