N,N-Dimethylaniline → 1-(3-Methoxy-2-methyl-4-pyridyl)piperazine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+.

Provenance & Evidence