Sodium Hydroxide → 3-(1-Methylpyrrolidin-2-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

1-methyl-3-nicotinoyl-2-pyrrolidone (20.4 g, 0.1 mol) was dissolved in a 6N hydrochloric acid (150 mL) The solution was heated to 135° C. to react for 8 h and then cooled to room temperature. The pH of the mixture was adjusted to 7 by using NaOH under an ice bath, and then potassium borohydride (5.3 g, 0.1 mol) was added therein and the temperature was back to room temperature for 2 h. 200 mL distilled water was added and the mixture was stream-distilled. The distilled water phase was concentrated till dry to give 12.2 g racemic nicotine. HPLC purity 98.4%; 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