Ethylenediamine → Tert-butyl 6-[(2-aminoethyl)amino]pyridine-3-carboxylate

HRID 2228600Notes

Reaction equation

HRID 2228600 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH2:15]([NH2:18])[CH2:16][NH2:17]>>[NH2:17][CH2:16][CH2:15][NH:18][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 11521348Tert-butyl 6-chloropyridine-3-carboxylate

Product 1

HCID 22142445Tert-butyl 6-[(2-aminoethyl)amino]pyridine-3-carboxylate

Procedure

The tert-butyl 6-chloropyridine-3-carboxylate was heated with ethylenediamine (20 mL) at 80° C. overnight. The solvent was removed in vacuo. The residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide solution. The aqueous layer was extracted a further three times with dichloromethane. The combined organic layers were washed with water, dried and concentrated in vacuo to give tert-butyl 6-[(2-aminoethyl)amino]pyridine-3-carboxylate. NMR (300 MHz, CDCl3): 8.70 (s, 1H), 7.95 (d, 1H), 6.40 (d, 1H), 3.42 (m, 2H), 2.96 (m, 2H), 1.70 (s, 9H)

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between dichloromethane and 2.5 M aqueous sodium hydroxide solution
  3. extractionThe aqueous layer was extracted a further three times with dichloromethane
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f38559519ec41b494415571ac036ee5
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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