Glycine → N,N-Bis[(pyridin-2-yl)methyl]glycine

HRID 254120Notes

Reaction equation

HRID 254120 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[NH2:10][CH2:11][C:12]([OH:14])=[O:13].[OH-].[Na+]>O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:10]([CH2:11][C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 15392583N,N-Bis[(pyridin-2-yl)methyl]glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloromethylpyridine hydrochloride (9.2 g, 8.53 mmol) and glycin (2 g, 26.6 mmol) were dissolved in water (30 mL) and stirred at room temperature for five days, with addition of 5 mol aqueous NaOH solution at intervals to maintain the pH at 8-10. The resulting dark red solution was extracted with ethyl acetate, neutralized with HCl and concentrated. The residue was dissolved in dichloromethane, and the insoluble sodium chloride was filtered. Pale yellow crystals formed from the filtrate, which were collected and dried under vacuum. Yield (2.87 g) (11.2 mmol, 42%). 1H NMR (CDCl3), 300 MHz): 3.39 (s, 2H), 3.98 (s, 4H), 7.06 (t, 2H), 7.30 (d, 2 h), 7.56 (t, 2H), 8.36 (d, 2H). 13C NMR (CD3OD, 300 MHz): 57.36 (C, CH2), 59.77 (2C, PyCH2), 124.77 (2CH, Py), 125.15 (2CH, Py), 139.00 (C, CH2), 149.76 (2CH, Py), 156.10 (2C, Py), 173.05 (C, CO2H).

Workup

  1. temperatureto maintain the pH at 8-10
  2. extractionThe resulting dark red solution was extracted with ethyl acetate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. filtrationthe insoluble sodium chloride was filtered
  6. customPale yellow crystals formed from the filtrate, which
  7. customwere collected
  8. customdried under vacuum
  9. customYield (2.87 g) (11.2 mmol, 42%)
  10. custom3.39 (s, 2H), 3.98 (s, 4H), 7.06 (t, 2H), 7.30 (d, 2 h), 7.56 (t, 2H), 8.36 (d, 2H)

Sources & evidence

ORD record
ord-0e0626d5337c4c6e8773461d415c4420
Source dataset
uspto-grants-2011_01
Patent number
US07875258B2

Reaction notes

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