Nitrogen → HCID 54555949, compound

Participants

Reaction Steps

To a RB flask equipped with magnetic stirring bar, condenser, Dean-Stark trap and N2 bubbler was added 10-chloroanthracene-9-carbaldehyde (Aldrich, 50.0 g, 0.208 mol, 2-amino-2-methyl-1,3-propanediol (Aldrich, 43.7 g, 0.415 mol) p-toluenesulfonic acid monohydrate (Aldrich, 3.98 g, 20.8 mmol) and PhCH3 (750 mL). The mixture was refluxed for 3.5 h with azeotropic removal of H2O. Most of the PhCH3 was then distilled from the mixture. The mixture was then cooled to 0° and diluted with abs. EtOH (700 mL). Solid NaBH4 (MCB Manufacturing Chemists Inc. 2909 Highland Ave., Cincinnati, OH, 45212, 9.55 g, 0.252 mol) was then added to the reaction mixture in 0.5 g portions. The reaction was then allowed to warm to RT and stirred overnight. A 1N NaOH solution (10 mL) was then added to the reaction mixture and the solvents removed by rotary evaporation. The solid was then shaken with several portions of 1N NaOH solution (4×300 mL) and filtered. The yellow solid was washed with H2O (3×500 mL) and sucked semidry. The solid was then dissolved in a mixture of CH3OH (800 mL) and CH3SO3H (Aldrich, 19.3 g, 0.20 mol, 13.0 mL) filtered and diluted to 2.5 L with Et2O. Two further crystallizations gave 2-(((10-chloro-9-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol methanesulfonate mp 234°-235° (dec.), (CH3OH/Et2O), (C, H, Cl, N, S).

Provenance & Evidence