Cyclopentanone → 13-aza-6-oxadispiro[4.2.4.I]tridecane

Participants

Reaction Steps

A solution of 1-hydroxymethylcyclopentanamine (Method B1c; 263 g, 2.3 mol) and cyclopentanone (220 mL, 1.3 mol, 1.1 equiv.) in toluene (2.7 L) was heated at the reflux temp. with azeotropic removal of water until the theoretical amount of water had been collected (41.4 mL). The reaction mixture was concentrated to 700 mL by simple distillation, then cooled to room temp. and concentrated to constant weight under reduced pressure to give 6-aza-12-oxadispiro[4.1.4.2]tridecane (414 g, 100%) as a pale yellow oil: 1H NMR (CDCl3) δ1.55-1.89 (m, 17H), 3.60 (s, 2H).

Provenance & Evidence