Ethylenediamine → N-(4-Ethoxy-2-pyridyl)ethane-1,2-diamine

HRID 631795Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13].C(=O)([O-])[O-].[K+].[K+]>>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:13][CH2:12][CH2:11][NH2:14])[CH:7]=1)[CH3:10]

Participants

Reactant 3

HCID 3301Ethylenediamine

HCID 11430Potassium Carbonate

HCID 5651602-Bromo-4-ethoxypyridine

Product 1

HCID 89825952N-(4-Ethoxy-2-pyridyl)ethane-1,2-diamineYield 64%

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-bromo-4-ethoxypyridine (500 mg, 2.475 mmol), ethane-1,2-diamine (9.9 ml, 150 mmol) and potassium carbonate (685 mg, 4.95 mmol) was stirred under microwave heating at 140° C. for 2 hours. The reaction mixture was filtered, the remaining solids were rinsed with ethanol and the combined filtrates were concentrated under reduced pressure and purified by flash column chromatography (silica, gradient of 2%-100% 7N NH3 in MEOH in DCM) to yield 287 mg of a solid (1.584 mmol, 64%). MS(ESI) m/z=182.0 [M+1]+.

Workup

filtrationThe reaction mixture was filtered
washthe remaining solids were rinsed with ethanol
concentrationthe combined filtrates were concentrated under reduced pressure
custompurified by flash column chromatography (silica, gradient of 2%-100% 7N NH3 in MEOH in DCM)

Sources & evidence

ORD record: ord-edbf27583e6b4909ac041ab012341622
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321724B2

Reaction notes

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