Sodium Iodide → (2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

HRID 68995Notes

Reaction equation

HRID 68995 reaction equation
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:15]=1.C(N(C(C)C)C(C)C)C>O.CN(C=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][N:22]([CH2:23][C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH2:4][CH2:5][CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 60761584(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

Product 1

HCID 66960900(2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium iodide (1.5 g) was added to a DMF solution (20 ml) of 2-(3-bromopropoxy)tetrahydropyran (0.85 ml). The mixture was stirred at 70° C. for 7 hours. The reaction mixture was cooled to room temperature. (2-Pyridin-3-yl-ethyl)-pyridin-4-ylmethyl-amine (1.28 g), and N-ethyldiisopropylamine (1.3 ml) were added thereto. The mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water and then saturated saline, and dried with anhydrous sodium sulfate. After condensation under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1). The purified product was condensed under reduced pressure to give the title compound (236 mg) as a colorless oily matter.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with water
  5. dry with materialsaturated saline, and dried with anhydrous sodium sulfate
  6. customAfter condensation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1)
  8. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-da1ec6637df4444ba16a033822c3096f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…