Dimethylformamide → (3-Chloropropyl)-(2-pyridin-3-ylethyl)pyridin-4-ylmethylamine

HRID 68997Notes

Reaction equation

HRID 68997 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:2]=1.C(N(C(C)C)C(C)C)C.CN(C=O)C.[Cl:31][CH2:32][CH2:33][CH2:34]I>O>[Cl:31][CH2:32][CH2:33][CH2:34][N:9]([CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 813631-Chloro-3-iodopropaneHCID 81531DiisopropylethylamineHCID 60761584(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamine

Product 1

HCID 66961018(3-Chloropropyl)-(2-pyridin-3-ylethyl)pyridin-4-ylmethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2-Pyridin-3-yl-ethyl)-pyridin-4-ylmethyl-amine (210 mg) and N-ethyldiisopropylamine (0.34 ml) were added to a DMF solution (2 ml) of 1-chloro-3-iodopropane (0.16 ml). 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 (74 mg) as a colorless oily matter.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water
  3. dry with materialsaturated saline, and dried with anhydrous sodium sulfate
  4. customAfter condensation under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→4:1)
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-114ce8ebf149461e96c1a1b402fcc09f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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