Acetyl chloride → 2-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol diacetate

Participants

Reaction Steps

A mixture of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride (1B, 5.0 g, 13.1 mmol) and acetylchloride (Aldrich, 5.0 mL, 70.3 mmol) was refluxed in dry THF (200 mL) under N2 for 12 h. The reaction mixture was poured into a satd. NaHCO3 solution (500 mL) and extracted with EtOAc (3×500 mL). The EtOAc layers were combined, dried (K2CO3) and filtered to give a slightly yellow liquid. The solvent was removed to give an off-white solid. This was recrystallized 3× from PhCH3 /hexane (1:1). After filtration and drying, 3.67 g (65.2%) of 2-((6-chrysenylmethyl)amino)-2-methyl-1,3-propanediol diacetate was obtained mp 136°-137.5°, (C,H,N).

Provenance & Evidence