Reaktion #46682

Reaktionsgleichung

sodium hydrogencarbonate

2-(1-adamantyl)-N-pentylethylamine hydrochloride

4-(3-aminopropyl)pyridine

1,1′-thiocarbonyldiimidazole

→

compound

Ausbeute 24.0%

1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]thiourea

Ausbeute 24.0%

Lösungsmittel

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe whole was refluxed for 2.5 hours
2. 2
   SonstigeAfter separation
3. 3
   Waschenthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml)
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   EinengenThen the obtained concentrate
7. 7
   Sonstigewas purified by silica gel column chromatography

Vorschrift

A solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1, 0.24 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to 1,1′-thiocarbonyldiimidazole (0.31 g, 1.8 mmol) under a nitrogen atmosphere, and the mixture was stirred at room temperature. After one hour, a solution of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 0.50 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to the mixture, and the whole was refluxed for 2.5 hours. The reaction mixture was allowed to stand, and then ethyl acetate (50 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the reaction mixture. After separation, the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give the target compound (0.18 g, 24%).

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