2-(Adamantan-1-yl)-N-methylethan-1-amine → HCID 21974209, compound

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.

1. waitAfter eight minutes
2. washthe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (40 ml) twice
3. dry with materiala saturated aqueous sodium chloride solution (40 ml) successively, and the organic layer was dried over magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was purified by silica gel column chromatography

ORD record

ord-b74c24f4aee8402686e3d33d80ff1ca1

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923461B2