Ethylenediamine → N-[2-(2-Methyl-1,3-dioxolan-2-yl)-4-pyridyl]ethane-1,2-diamine

HRID 333062Notes

Reaction equation

HRID 333062 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)[CH:3]=1.[NH2:14][CH2:15][CH2:16][NH2:17]>>[CH3:13][C:8]1([C:4]2[CH:3]=[C:2]([NH:14][CH2:15][CH2:16][NH2:17])[CH:7]=[CH:6][N:5]=2)[O:12][CH2:11][CH2:10][O:9]1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 668355144-Chloro-2-(2-methyl-1,3-dioxolan-2-yl)pyridine

Product 1

HCID 66835538N-[2-(2-Methyl-1,3-dioxolan-2-yl)-4-pyridyl]ethane-1,2-diamineYield 95.2%

Conditions

Temperature
180 °C

Procedure

4-Chloro-2-(2-methyl-1,3-dioxolan-2-yl)pyridine (500 mg, 2.5 mmol) was mixed with 1,2-diaminoethane (1.09 ml, 26.2 mmol) and stirred in a closed vessel at 180° C. with microwave heating for 30 minutes in two batches. The mixture was evaporated to dryness, the solid residue was washed with acetone. The washing solution was evaporated to dryness and this solid residue was washed with acetonitrile. The solid residues were combined and dried under reduced pressure to yield 531 mg of a solid (2.38 mmol, 95%). MS (APCI) m/z=224.1 [M+H]+.

Workup

  1. temperatureheating for 30 minutes in two batches
  2. customThe mixture was evaporated to dryness
  3. washthe solid residue was washed with acetone
  4. customThe washing solution was evaporated to dryness
  5. washthis solid residue was washed with acetonitrile
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-bec392ac1a5847c486292900401e513b
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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