N,N'-Dimethylethylenediamine → HCID 61709050, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-N-(2,4,4-trimethylpentan-2-yl)pyridin-2-amine (7.5 g, 260 mmol), sodium azide (5.07 g, 780 mmol), CuI (1.4 g, 7.8 mmol), N,N′-dimethylethane-1,2-diamine (1.3 g, 15 mmol) in dimethylsulfoxide (150 mL) was heated in a sealed reaction vessel at 90° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (500 mL), saturated ammonium chloride (1000 mL) and stirred for 1 hour. The organic layer was separated and the aqueous layer was again extracted with ethyl acetate (3×300 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated to give brown sticky mass which was purified by silica gel column chromatography using methanol and dichloromethane as eluent to yield 2 g (34%) of N2-(2,4,4-trimethylpentan-2-yl)pyridine-2,4-diamine.

Provenance & Evidence