반응 #11568

반응 방정식

N-methyl-3-(4-pyridyl)propylamine

diisopropylethylamine

2-(1-adamantyl)-N-methylethylamine

diisopropylethylamine

triphosgene

→

titled compound

수율 141.6%

1-[2-(1-Adamantyl)ethyl]-1,3-dimethyl-3-[3-(4-pyridyl)propyl]urea

수율 141.6%

용매

dichloromethane

dichloromethane

dichloromethane

diethyl ether

반응 조건

후처리

1. 1
   workup.WAITAfter eight minutes
2. 2
   세척the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (40 ml) twice
3. 3
   건조a saturated aqueous sodium chloride solution (40 ml) successively, and the organic layer was dried over magnesium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   기타the residue was purified by silica gel column chromatography

실험 절차

A solution of triphosgene (190 mg, 0.640 mmol) in dichloromethane (6.0 ml) was stirred at room temperature under a nitrogen atmosphere. A solution of 2-(1-adamantyl)-N-methylethylamine (Intermediate No. 3-1) (330 mg, 1.71 mmol) and diisopropylethylamine (0.357 ml, 2.05 mmol) in dichloromethane (6.0 ml) was added dropwise thereto over 17 minutes. After eight minutes, a solution of N-methyl-3-(4-pyridyl)propylamine (Intermediate No. 3-3) (264 mg, 1.78 mmol) and diisopropylethylamine (0.357 ml, 2.05 mmol) in dichloromethane (5.1 ml) was added to the mixture at a stretch, and the whole was stirred for 20 hours. The reaction mixture was diluted with diethyl ether (40 ml), the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (40 ml) twice and a saturated aqueous sodium chloride solution (40 ml) successively, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 335 mg (54%) of the titled compound.

출처