4-Vinylpyridine → Bis[2-(4-pyridyl)ethyl]amine

HRID 613353Notes

Reaction equation

HRID 613353 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].[Cl-].[NH4+:10]>CO>[N:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][NH:10][CH2:2][CH2:1][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 75024-VinylpyridineHCID 25517Ammonium Chloride

Product 1

HCID 416637Bis[2-(4-pyridyl)ethyl]amineYield 16.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-vinylpyridine (10.0 g, 95.1 mmole) and ammonium chloride (5.1 g, 95.1 mmole) in MeOH (90 mL) was heated to reflux under argon for 27 h. The resulting mixture was filtered and the filtrate was concentrated on the rotavap. The residue was dissolved in H2O (200 mL), and the solution was basified to pH 10.5 using 2 N NaOH. CH2Cl2 extraction (3×100 mL), drying (MgSO4), and concentration gave a yellow oil (5.73 g, 49% crude). 2.9 g of this oil was chromatographed on silica gel (12% MeOH/CH2Cl2) to afford the title compound as a yellow oil (1.81 g, 16%). MS (ES) m/e 228 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 27 h
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated on the rotavap
  5. dissolutionThe residue was dissolved in H2O (200 mL)
  6. extractionCH2Cl2 extraction (3×100 mL)
  7. customdrying
  8. concentration(MgSO4), and concentration
  9. customgave a yellow oil (5.73 g, 49% crude)
  10. custom2.9 g of this oil was chromatographed on silica gel (12% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4e64e160491042c1993bbf039cff0387
Source dataset
uspto-grants-1999_12
Patent number
US06008214

Reaction notes

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