Methylamine → 2-Chloro-6-[4-(methylamino)piperidin-1-yl]isonicotinonitrile

Participants

Reaction Steps

Methylamine (2.65 ml, 5.3 mmol) was added to a solution of 2-chloro-6-(4-oxopiperidin-1-yl)isonicotinonitrile (Intermediate 26; 500 mg, 2.12 mmol) in anhydrous THF (4 ml). The mixture was stirred for 30 minutes and sodium triacetoxyborohydride (674 mg, 3.18 mmol) was added. The mixture was stirred at room temperature for 18 h, then concentrated in vacuo, diluted with EtOAc and washed with 1 N NaOH, water and brine. The organic phase was dried over Na2SO4 then concentrated in vacuo to give a brown oil which was dried under vacuum to yield the title compound (507 mg).

Provenance & Evidence