Methyl iodide → 2-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 18410

Reaction equation

HRID 18410 reaction equation
[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15]Br)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].CI.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)C.O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15][NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 574798992-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

Product 1

HCID 574798982-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamideYield 41.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Next, 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, 3.5 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g, 11 mmol), methyl iodide (1.6 g, 11 mmol) and 4-(2-aminoethyl)pyridine (0.43 g, 3.5 mmol) were added to the solution, and the mixture was stirred at an external temperature of 75° C. overnight. Water (100 ml) and diethyl ether (100 ml) were added to the reaction mixture to distribute it. The diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively, 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 (0.6 g, 40%) as an oily matter.

Workup

  1. washThe diethyl ether layer was washed with water (70 ml) twice
  2. dry with materiala saturated aqueous sodium chloride solution (120 ml) once successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. concentrationThen the obtained concentrate
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3013360acf7497db699e1a1d3e6ad1d
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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