Hydrochloric Acid → 1-(chloromethyl)-1-(cyclopentylamino)cyclopentane HCl salt

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(cyclopentylamino)-1-(hydroxymethyl)cyclopentane (Method B1c; 140 g, 0.76 mol, 1.0 equiv.) in toluene (1.4 L). was added SOCl2 (84 mL) over a period of 15 min. After the addition of SOCl2 was complete the reaction mixture, which had already warmed to 40° C., was heated at 60° C. overnight. The resulting solution was cooled to room temp. and treated with HCl (4N in p-dioxane, 100 mL), and the reaction was heated to 60° C. for 3 h then stirred at room temp. overnight. The resulting mixture was concentrated to half of the original volume under reduced pressure, at which time a precipitate began to form. The resulting slurry was diluted with Et2O and allowed stir for 4 h. The resulting precipitate was filtered and washed with Et2O (2×50 mL) to yield 1-(chloromethyl)-1-(cyclopentylamino)cyclopentane HCl salt as an off-white powder (125 g, 70%): 1H NMR (CDCl3) δ1.53-1.66 (m, 4H), 1.76-1.94 (m, 2H) 1.95-2.22 (m, 10H), 2.28-2.34 (m, 2H), 3.40 (s, 2H), 3.63-3.73 (m, 1H).

Provenance & Evidence