Hydrochloric Acid → 1-[2-(1-Adamantyl)ethyl]-1-(2-aminoethyl)-3-[3-(4-pyridyl)propyl]urea
Reaction equation
Cl.C([NH:5][CH2:6][CH2:7][N:8]([CH2:21][CH2:22][C:23]12[CH2:32][CH:27]3[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]3)[CH2:24]1)[CH2:30]2)[C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:10])(=O)C.[OH-].[Na+].C(Cl)(Cl)Cl>CO.O>[C:23]12([CH2:22][CH2:21][N:8]([CH2:7][CH2:6][NH2:5])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[O:10])[CH2:30][CH:29]3[CH2:28][CH:27]([CH2:26][CH:25]([CH2:31]3)[CH2:24]1)[CH2:32]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Under ice-cooling, 6 N hydrochloric acid (15 ml) was added to a solution of 1-[2-(acetylamino)ethyl]-1-[2-(1-adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-103, 1.02 g, 2.39 mmol) in methanol (10 ml), and the mixture was heated at 90° C. with stirring for three days. The reaction mixture was neutralized with a 1 N aqueous sodium hydroxide solution (10 ml), and the whole was distributed between chloroform (50 ml) and water (10 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the target compound (200 mg, 21.7%) as an oily matter.
Workup
- temperatureUnder ice-cooling
- washThe organic layer was washed with a saturated aqueous sodium chloride solution (50 ml)
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-5c2f3cc5c5d342e2ad09405208497aff
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741346B2
Reaction notes
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