Ammonia → 1-(2,5-Dimethylpyridin-4-yl)piperidin-4-amine

Participants

Reaction Conditions

Reaction Steps

A mixture 4-chloro-2,5-dimethyl-pyridine 1-oxide (200 mg, 1.41 mmol), Boc-4-aminopiperidine (311 mg, 1.55 mmol) and N,N-diisopropyl ethyl amine (484 μL, 2.82 mmol) in sulfolane (1 mL) was heated to 160° C. for 30 minutes in a microwave oven followed by heating to 220° C. for 30 minutes. After the addition of aqueous hydrochloric acid (25% in water, 0.5 mL) the mixture was stirred for 18 h at ambient temperature. It was treated with ammonia in methanol and concentrated. Purification by chromatography (SiO2, dichloromethane/methanol/ammonia=95:4.5:0.5 to 90:9:1) afforded the title compound (99 mg, 40%) as a light brown oil.

Provenance & Evidence