1,1'-Carbonyldiimidazole → 1-(2-(1-Adamantyl)ethyl)-1-pentyl-3-(3-(4-pyridyl)propyl)urea

HRID 11462Notes

Reaction equation

HRID 11462 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.Cl.[C:24]12([CH2:34][CH2:35][NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>O1CCCC1.C(OCC)(=O)C>[C:24]12([CH2:34][CH2:35][N:36]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:1]([NH:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[O:2])[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143474663-(Pyridin-4-yl)propan-1-amineHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Product 1

HCID 101585621-(2-(1-Adamantyl)ethyl)-1-pentyl-3-(3-(4-pyridyl)propyl)ureaYield 73.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-Carbonyldiimidazole (427 mg, 2.63 mmol) was added to a solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1) (285 mg, 2.09 mmol) in tetrahydrofuran (10 ml), and the mixture was stirred at room temperature for 20 minutes. 2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (571 mg, 2.00 mmol) was added to the mixture, and the whole was refluxed for one hour. The reaction mixture was diluted with ethyl acetate (50 ml), the whole was washed with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and a saturated aqueous sodium chloride solution (50 ml) successively, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the precipitated solid was washed with diisopropyl ether and filtered off to give 606 mg (73%) of the titled compound.

Workup

  1. temperaturethe whole was refluxed for one hour
  2. washthe whole was washed with a saturated aqueous sodium hydrogencarbonate solution (50 ml)
  3. dry with materiala saturated aqueous sodium chloride solution (50 ml) successively, and the organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe precipitated solid was washed with diisopropyl ether
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-0eb80d802e664db3981256e4c180b24f
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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