Water → 3-(1-Methylpyrrolidin-2-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

1-methyl-3-nicotinoyl-2-pyrrolidone (11.3 g, 0.055 mol) was dissolved in a 6N hydrochloric acid (125 mL) The solution was heated at 135° C. in an oil bath for 40 h and then cooled to room temperature. The pH of the mixture was adjusted to 8 by using 4 mol/L sodium hydroxideunder an ice-water bath, and then sodium borohydride (2.4 g) was added therein under ice-water bath. The mixture was stirred for 1.5 h after the ice-water bath was removed. The reaction solution was extracted with dichloromethane, dried and concentrated to obtain a crude product as a yellowish oil. 100 mL water was added and the mixture was stream-distilled directly. After the water was extracted with petroleum ether, the extract was dried and concentrated to obtain an oily product (7.8 g, yield 71%). HPLC purity 98.2%. 1H NMR (CDCl3, 300 MHz) δ: 8.52 (d, 1H), 8.48 (dd, 1H), 7.69 (dt, 1H), 7.25 (dd, 1H), 3.23 (t, 1H), 3.07 (t, 1H), 2.29 (m, 1H), 2.16 (s, 3H), 1.90-2.04 (m, 2H), 1.65-1.88 (m, 2H); ESI-MS 163.4 (M+H).

Provenance & Evidence