tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamate → N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)

Participants

Reaction Steps

4 N HCl/dioxane (54 mL) was added in a stream to a solution of 2-[[2-(tert-butoxycarbonyl)amino-1-ethyl]amino]pyridine (5.09 g, 21.45 mmole) in anhydrous CH2Cl2 (54 mL) at 0° C. under argon, then the mixture was warmed to RT. After 2 hr, the mixture was cooled to 0° C. and suction filtered. The solid was washed extensively with anhydrous Et2O and dried in high vacuum at 40° C. to afford the title compound (4.27 g, 95%) as an off-white, somewhat hygroscopic solid: 1H NMR (400 MHz, CD3OD) δ7.99-8.07 (m, 1 H), 7.92-7.98 (m, 1 H), 7.19 (d, J=9.1 Hz, 1 H), 6.98-7.04 (m, 1 H), 3.76 (t,J=6.2 Hz, 2 H). 3.27 (t, J=6.2 Hz, 2 H, partially obscured by residual solvent signal); MS (ES) m/e 138 (M+H)+.

Provenance & Evidence