Tert-Butylamine → 3-(tert-Butylamino)propylsulfonic acid

Participants

Reaction Steps

To a solution of 1,3-propanesultone (20 g, 0.164 g) in toluene (100 mL) was added tert-butylamine (90 mL, 62.1 g, 0.85 mol). The mixture was stirred under gentle reflux for 1 hour. The precipitate was filtered, washed with diethyl ether and dried at 20-25° C. Yield 3-(tert-butylamino)propylsulfonic acid 32 g (approximately 100%), as white microcrystals, mp above 280° C., 1H NMR (D2O) δ 1.33 (s, 9H), 2.07 (p, J=7.6 Hz, 2H), 2.99 (t, J=7.6 Hz, 2H), 3.15 (t, J=7.7 Hz, 2H); 13C NMR δ 21.3, 24.3, 39.4, 47.4, 56.5.

Provenance & Evidence