Water → HCID 21959661, compound

Participants

Reaction Conditions

Reaction Steps

1-Methylpiperidin-4-ol (0.457 g, 3.97 mmol) was dissolved in 5 mL of DMSO under argon and NaH (0.173 g, 3.97 mmol) was added. The reaction mixture was stirred at ambient temperature for 3 h and 30 min at 60° C. The mixture was allowed to cool and 2-chloro-4 pyridinecarbonitrile (0.500 g, 3.97 mmol) was added. The mixture was stirred for 2 h at ambient temperature and subsequently poured into 100 mL of water, extracted three times with EtOAc. The combined organic layer washed with water, dried over Na2SO4 and evaporated. The crude product was purified by preparative HPLC (Kromasil C8 50×250 mm, CH3CN/0, 2% HOAc 5/95-50/50). The product was freeze dried from water. Yield: 0.250 g (32%). 1H NMR (500 MHz, CD3OD) δ8.32 (d, 1H), 7.19 (dd, 1H), 7.12 (bs, 1H), 5.14 (m, 1H), 2.75 (m, 2H), 2.38 (m, 2H), 2.32 (s, 3H), 2.06 (m, 2H), 1.84 (m, 2H).

Provenance & Evidence