2-Bromopyridine → N1-(Phenylmethyl)-N2-2-pyridinyl-1,2-ethanediamine

HRID 2213047Notes

Reaction equation

HRID 2213047 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1([CH2:14][NH:15][CH2:16][CH2:17][NH2:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)(=O)C>[C:8]1([CH2:14][NH:15][CH2:16][CH2:17][NH:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 77801N-Benzylethylenediamine

Product 1

HCID 21955371N1-(Phenylmethyl)-N2-2-pyridinyl-1,2-ethanediamineYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromopyridine (6.1 mL, 64 mmol) was added to N-(phenylmethyl)-1,2-ethanediamine (50 ml, 322 mmol) and the mixture was heated at 130–140° C. for 2 hours. The mixture was cooled, diluted with ethyl acetate (500 mL), washed with water (3×150 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:8:1), to give the title compound as a yellow oil (5.7 g, 40%). m/z (ES+) 228 (M+1).

Workup

  1. temperaturethe mixture was heated at 130–140° C. for 2 hours
  2. temperatureThe mixture was cooled
  3. washwashed with water (3×150 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with CH2Cl2/MeOH/NH3(Aq.) (90:8:1)

Sources & evidence

ORD record
ord-2bb10aa213f94944b01a6b8dcab2db78
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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