Ethanol → 1,3-Propanediol, 2-((1-fluoranthenylmethyl)amino)-2-methyl-, hydrochloride

Participants

Reaction Steps

To a RB flask equipped with magnetic stirring bar, condenser and N2 inlet line with bubbler was added crude 1-chloromethylfluoranthene (3C, 13.01 g, 52 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich, 5.46 g, 52 mmol), K2CO3 (MCB, 14.37 g, 0.104 mol) and abs. EtOH (300 mL). The reaction was stirred at reflux overnight, filtered hot, and the solvent removed by rotary evaporation to give a crude dark oil. This was acidified with 1N HCl and dissolved in H2O, filtered, basified with 5N NaOH solution and filtered to give a crude white solide. The material was dissolved in ethanolic HCl solution, filtered and precipitated with Et2O. Filtration followed by crystallization (abs. EtOH/Et2O, 1:4) gave after filtration and drying a 43.8% yield of 2-[(1-fluorantheneylmethyl)amino]-2-methyl-1,3-propanediol hydrochloride 0.3 H2O, mp 185-188 (dec), (C,H,N,Cl).

Provenance & Evidence