Hydrochloric Acid → HCID 18700424, compound

Participants

Reaction Steps

In a 12 l round bottomed flask combine isonipecotic acid (1226 g, 9.49 moles), 37% formaldehyde (850 ml) and absolute ethanol (5.0 l) and stir for thirty minutes. Sodium cyanide (470 g, 9.49 moles) is added and the reaction stirred at ambient temperature overnight. Absolute ethanol (1.3 l) and 12 M hydrochloric acid (795 ml) is added and the suspension stirred for four hours. The product is collected by vacuum filtration, washed thrice with methyl-t-butylether (3.0 l) and dried at 25 in Hg overnight to give N-cyanomethyl isonipecotic acid (1909 g, 8.05 moles) as a 1:1 mixture with sodium chloride. 1H NMR (400 MHz, d6 DMSO) d 1.55 (m, 2H), 1.82 (m, 2H), 2.18 (m, 3H), 2.72 (m, 2H), 3.71 (s, 2H), 12.30 (bs, 1H).

Provenance & Evidence