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

HRID 2358892Notes

Reaction equation

HRID 2358892 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, 2h), 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%)

Sources & evidence

ORD record
ord-838f7654a7c145f6a1656e708286d9d8
Source dataset
uspto-grants-2014_04
Patent number
US08685369B2

Reaction notes

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