Methyl iodide → (R)-1-[2-(4-Pyridyl)ethyl]-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide hydrochloride

HRID 11482Notes

Reaction equation

HRID 11482 reaction equation
Cl.[C:2]12([CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([C@H:17]3[CH2:21][CH2:20][CH2:19][NH:18]3)=[O:16])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(=O)([O-])[O-].[K+].[K+].CI.Cl.[Cl:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1.[OH-].[Na+]>CN(C)C=O.C(OCC)C>[ClH:36].[C:2]12([CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([C@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)=[O:16])[CH2:9][CH:8]3[CH2:10][CH:4]([CH2:5][CH:6]([CH2:7]3)[CH2:11]1)[CH2:3]2

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 124817414-(2-Chloroethyl)pyridine hydrochlorideHCID 67118563HCID 67118563, compound

Product 1

HCID 67118947(R)-1-[2-(4-Pyridyl)ethyl]-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide hydrochlorideYield 47%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Next, (R)-2-pyrrolidinecarboxylic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide hydrochloride (1.4 g, 3.7 mmol) was dissolved in anhydrous N,N-dimethylformamide (40 ml), potassium carbonate (2.6 g, 19 mmol), methyl iodide (1.7 g, 11 mmol) and 4-(2-chloroethyl)pyridine hydrochloride (0.70 g, 3.7 mmol) were added to the solution, and the mixture was stirred at an external temperature of 80° C. overnight. A 2 N aqueous sodium hydroxide solution (70 ml) and diethyl ether (70 ml) were added to the reaction mixture, the reaction mixture was distributed, and the diethyl ether layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) successively and dried over anhydrous magnesium sulfate. The diethyl ether layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.80 g (47%) of the titled compound as an oily matter.

Workup

  1. washthe diethyl ether layer was washed with water (70 ml)
  2. dry with materiala saturated aqueous sodium chloride solution (70 ml) successively and dried over anhydrous magnesium sulfate
  3. concentrationThe diethyl ether layer was concentrated under reduced pressure
  4. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-69caa58474a641298e579f0a71042a19
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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